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Mephedrone

PubChem CID
45266826
Structure
Mephedrone_small.png
Mephedrone_3D_Structure.png
Molecular Formula
Synonyms
  • mephedrone
  • 4-methylmethcathinone
  • Meow meow
  • 4-MMC
  • M-CAT
Molecular Weight
177.24 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2010-05-07
  • Modify:
    2025-01-18
Description
Mephedrone is an aromatic ketone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes. It has a role as a xenobiotic and an environmental contaminant. It is a member of amphetamines, an aromatic ketone and a secondary amino compound. It is functionally related to a propiophenone.
4-methylmethcathinone is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.
Mephedrone has been investigated in Alcohol-Related Disorders and Amphetamine-Related Disorders.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Mephedrone.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Me-DL-Ala-Ph(4-Me)
Sequence
A

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

2-(methylamino)-1-(4-methylphenyl)propan-1-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

YELGFTGWJGBAQU-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

CC1=CC=C(C=C1)C(=O)C(C)NC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C11H15NO
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 ChEMBL ID

3.3.6 DEA Code Number

1248 (DEA schedule I controlled substance)

3.3.7 DrugBank ID

3.3.8 DSSTox Substance ID

3.3.9 HMDB ID

3.3.10 KEGG ID

3.3.11 Metabolomics Workbench ID

3.3.12 Nikkaji Number

3.3.13 PharmGKB ID

3.3.14 Pharos Ligand ID

3.3.15 Wikidata

3.3.16 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 4-methylmethcathinone
  • 4-MMC compound
  • beta-keto-4-methylmethamphetamine
  • bk-4-methylmethamphetamine
  • mephedrone
  • MMCAT compound

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
177.24 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
177.115364102 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
177.115364102 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
29.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
171
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Color / Form

Fine-white to off-white or slightly colored powder ... also found in tablet or capsule form
US DEA; Drugs of Abuse. 2011 Edition. A DEA Resource Guide. US Dept Justice, Drug Enforcement Admin. Available from, as of Jun 23, 2011: https://www.justice.gov/dea/pubs/drugs_of_abuse.pdf

4.2.2 Collision Cross Section

143.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
143.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

133.88 Ų [M+H-H2O]+

145.51 Ų [M+H]+

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

4.3 Chemical Classes

4.3.1 Drugs

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
S58 | PSYCHOCANNAB | Synthetic Cannabinoids and Psychoactive Compounds | DOI:10.5281/zenodo.3247723
Pharmaceuticals -> Illicit drugs
S56 | UOATARGPHARMA | Target Pharmaceutical/Drug List from University of Athens | DOI:10.5281/zenodo.3248837
4.3.1.1 Human Drugs
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 5
View All
NIST Number
378823
Library
Main library
Total Peaks
54
m/z Top Peak
58
m/z 2nd Highest
91
m/z 3rd Highest
56
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2 of 5
View All
NIST Number
386262
Library
Replicate library
Total Peaks
73
m/z Top Peak
58
m/z 2nd Highest
91
m/z 3rd Highest
56
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5.2.2 MS-MS

1 of 7
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

145.0887 100

144.0809 22.06

160.1121 21.29

119.0856 20.83

91.0543 4.24

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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

145.0886 100

144.0809 77.35

119.0856 24.62

91.0543 15.40

130.0652 8

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5.2.3 LC-MS

1 of 18
View All
Authors
Nikiforos Alygizakis, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
RAMP 17.2-25.8 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.657 min
Precursor m/z
178.1226
Precursor Adduct
[M+H]+
Top 5 Peaks

145.0881 999

160.1116 585

144.0802 333

119.0856 160

91.0536 73

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License
CC BY
2 of 18
View All
Authors
Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
LTQ Orbitrap XL Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35 % (nominal)
Fragmentation Mode
CID
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
4.3 min
Precursor m/z
178.1226
Precursor Adduct
[M+H]+
Top 5 Peaks

160.1123 999

178.1225 60

147.0806 48

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License
CC BY

5.3 IR Spectra

5.3.1 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Film
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
Free base of 15657
Lot Number
Free base of 0492770-1
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Film
Source of Spectrum
Forensic Spectral Research
Source of Sample
Lipomed AG
Catalog Number
Free base of MCA-835-HC-1LA
Lot Number
Free base of 835.HC.1LA
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Drug and Medication Information

8.1 Drug Indication

8.2 Clinical Trials

8.2.1 ClinicalTrials.gov

8.3 DEA Drug and Chemical Information

4-Methylmethcathinone (Mephedrone)

(Street Names:4-MMC, meow meow, m-CAT, bounce, bubbles, mad cow)

8.3.1 DEA Controlled Substances

Substance
4-methylmethcathinone
Synonym(s)
Mephedrone
DEA Controlled Substances Code Number
1248
Controlled Substances Act Schedule
Schedule I - Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.
Class
Hallucinogenic substances

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

The main routes of administration for mephedrone are reported as snorting (nasal insufflation) and swallowing (oral ingestion), sometimes after dissolving with water. As mephedrone is primarily available in powder form, injecting use is reported but appears to be rare.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p29 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html

9.2 Metabolism / Metabolites

Rats administered a single 20 mg/kg dose of mephedrone by gastric intubation and urine was collected over a 24-hour period after mephedrone administration. In addition to mephedrone, the following metabolites were detected: nor-mephedrone, nor-dihydro mephedrone, hydroxytolyl mephedrone and nor-hydroxytolyl mephedrone. In a human urine sample submitted by a mephedrone user, a further metabolite, 4-carboxy-dihydro mephedrone was also detected. /It was/ postulated that the overlapping metabolic pathways that were thought to be responsible for these metabolites were as follows: N-demethylation to the primary amine (metabolites nor-mephedrone, nor-dihydro mephedrone and nor-hydroxytolyl mephedrone); reduction of the keto moiety to the respective alcohol (metabolites nordihydro mephedrone and 4-carboxy-dihydro mephedrone); oxidation of the tolyl moiety to the corresponding alcohol (metabolites hydroxytolyl mephedrone and nor-hydroxytolyl mephedrone). It is thought that the hydroxytolyl mephedrone and nor-hydroxytolyl mephedrone metabolites are partly excreted as glucuronides and sulfates.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p56 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html
Mephedrone is metabolized by a number of pathways to the following metabolites: nor-mephedrone, nor-dihydro mephedrone, nor-hydroxytolyl mephedrone, 4-carboxy-dihydro mephedrone, hydroxytolyl mephedrone. It is thought that the hydroxytolyl mephedrone and nor-hydroxytolyl mephedrone metabolites are partly excreted as glucuronide and sulfate conjugates.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p26 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html

9.3 Mechanism of Action

As with phenethylamines, in the absence of ring-substitution, cathinones behave predominantly as central nervous system (CNS) stimulants, although generally with a lower potency than the corresponding phenethylamine analogue. The lower potency is caused by the beta-keto group creating a more polar molecule with lower ability to cross the blood-brain barrier. In the presence of ring substitution, however, the properties are modified towards MDMA-like effects.
Europol (European Police Office) - European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Joint Report on a New Psychoactive Substance: 4-Methylmethcathinone (Mephedrone), p12 (2010). Available from, as of July 8, 2011: https://www.emcdda.europa.eu/html.cfm/index132196EN.html
There are no formal pharmacodynamic studies looking specifically at mephedrone. Based on its chemical structure, it is likely that it has a similar mechanism of action to other stimulant drugs (blocks reuptake of, and stimulates the release of stimulant neurotransmitters such as serotonin, dopamine and norepinephrine). This is further supported by the sympathomimetic effects (dilated pupils, tachycardia, hypertension, agitation) seen with mephedrone use that are similar to other stimulant drugs such as MDMA and cocaine.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p27 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html

9.4 Human Metabolite Information

9.4.1 Cellular Locations

Membrane

10 Use and Manufacturing

10.1 Uses

There are no known uses of mephedrone as a research, industrial, agricultural or cosmetic compound, despite it being marketed as 'plant feeder', 'bath salts' or 'research chemical'.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p58 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html
No approved medical uses in the United States
US DEA; Drugs of Abuse. 2011 Edition. A DEA Resource Guide. US Dept Justice, Drug Enforcement Admin. Available from, as of Jun 23, 2011: https://www.justice.gov/dea/pubs/drugs_of_abuse.pdf

10.1.1 Use Classification

Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

10.2 Formulations / Preparations

Some of the products found to contain synthetic cathinones /including mephedrone/ include, but are not limited to: Ivory Wave, Vanilla Sky, Energy 1, Explosion, Meow Meow, Bubbles, and others.
US DEA; Microgram Bulletin. Vol 44, No 4. April 2011. US Dept Just, Drug Enforcement Admin. Available from, as of July 9, 2011: https://www.justice.gov/dea/programs/forensicsci/microgram/mg2011/mg0411.pdf
In general, the quality and purity of mephedrone available to users is reported as high, and the analysis of seized and purchased mephedrone confirms this. However, some samples of mephedrone have been found to contain pharmaceutical agents (e.g. benzocaine, lidocaine, caffeine and paracetamol), other synthetic cathinones (e.g. butylone, methylone, ethylcathinone, fluoromethcathinone, methylenedioxypyrovalerone/MDPV) and/or other recreational drugs (e.g. MDMA, mCPP, ketamine).
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p34 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html

10.3 General Manufacturing Information

Synthetic cathinone ... designer drug market Psychoactive chemical structurally related to Schedule I stimulants
US DEA; Microgram Bulletin. Vol 44, No 4. April 2011. US Dept Just, Drug Enforcement Admin. Available from, as of Jun 23, 2011: https://www.justice.gov/dea/programs/forensicsci/microgram/mg2011/mg0411.pdf
Chemical analogue of methcathinone... a Schedule I controlled substance
US DEA; Drugs of Abuse. 2011 Edition. A DEA Resource Guide. US Dept Justice, Drug Enforcement Admin. Available from, as of Jun 23, 2011: https://www.justice.gov/dea/pubs/drugs_of_abuse.pdf

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Corrosive
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Skin Sens. 1 (100%)

Eye Dam. 1 (100%)

11.2 Accidental Release Measures

11.2.1 Disposal Methods

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

11.3 Regulatory Information

DEA Controlled Substances
DEA schedule I controlled substance

11.3.1 FDA Requirements

Schedule I shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. ... Temporary listing of substances subject to emergency scheduling. Any material, compound, mixture or preparation which contains any quantity of the following substances. Mephedron (DEA Code Number: 1248) is included on this list.
21 CFR 1380.11(g) (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 14, 2011: https://www.ecfr.gov

12 Toxicity

12.1 Toxicological Information

12.1.1 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

12.1.2 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ The desired psychological and behavioural effects reported by users include euphoria, general stimulation, enhanced music appreciation, elevated mood, decreased hostility, improved mental function and mild sexual stimulation. The latter effect was reported in 60 % of mephedrone users in the Mixmag survey. Overall, these effects seem comparable to that reported for other stimulant drugs such as MDMA, amphetamines and cocaine.
Europol (European Police Office) - European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Joint Report on a New Psychoactive Substance: 4-Methylmethcathinone (Mephedrone), p12 (2010). Available from, as of July 8, 2011: https://www.emcdda.europa.eu/html.cfm/index132196EN.html
/SIGNS AND SYMPTOMS/ Numerous symptoms are reported by users on Internet forums, these include: numbness and lack of tactile sensitivity, loss of appetite, insomnia, increased mean body temperature ('mephedrone sweat'), decrease in mean body temperature, bruxism, elevated heart rate and blood pressure, chest pain, nausea and vomiting, painful joints, discoloration of extremities/joints, abdominal pain, painful nasal drip with presence of blood, light headedness and dizziness, tremors and convulsions, headaches, cravings, nightmares, loss of concentration and memory loss, anxiety, dysphoria, depression, hallucinations, paranoia, fatigue and respiratory difficulties. It is not possible to determine the true use-dependence of these symptoms based on the user reports available and it is important to note that these are unconfirmed anecdotal reports from users.
Europol (European Police Office) - European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Joint Report on a New Psychoactive Substance: 4-Methylmethcathinone (Mephedrone), p13 (2010). Available from, as of July 8, 2011: https://www.emcdda.europa.eu/html.cfm/index132196EN.html
/SIGNS AND SYMPTOMS/ Users report on Internet forums that desired effects are typically seen within 15-45 minutes of oral ingestion. There are some reports of slower onset of action when mephedrone is taken orally on a full stomach. Following nasal insufflation, onset is reported by users to be within a few minutes and with peak effects within 30 minutes. Users report that the effects last approximately 2-3 hours and therefore that they may consume multiple doses during a session to prolong the duration of the desired effects. Reports from intravenous mephedrone users suggest that the high lasts approximately 10-15 minutes with an overall duration of desired effects of approximately 30 minutes.
Europol (European Police Office) - European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Joint Report on a New Psychoactive Substance: 4-Methylmethcathinone (Mephedrone), p12 (2010). Available from, as of July 8, 2011: https://www.emcdda.europa.eu/html.cfm/index132196EN.html
/SIGNS AND SYMPTOMS/ Some detailed information on the patterns of acute mephedrone toxicity is available from clinical case series from poisons information services and specialist hospitals in the United Kingdom and Sweden, including one series of analytically confirmed acute mephedrone toxicity from the United Kingdom. In this data, patients typically present with sympathomimetic features (dilated pupils, agitation, tachycardia, hypertension); severe clinical features such as chest pain, significant hypertension, arrhythmias and seizures have been reported in a small number of cases to date. Similar to other stimulant drugs, it is likely that the risk of toxicity is related to the dose of mephedrone used; however, there is insufficient information available from toxicity reports to determine a 'dose threshold' and/or whether particular routes of use are more likely to be associated with toxicity.
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) Risk Assessments; Report on the Risk Assessment of Mephedrone in the Framework of the Council Decision on New Psychoactive Substances, p30 (2011). Available from, as of July 7, 2011: https://www.emcdda.europa.eu/html.cfm/index116639EN.html
For more Human Toxicity Excerpts (Complete) data for Mephedrone (19 total), please visit the HSDB record page.

12.1.3 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Neurotoxicity/ The designer drug mephedrone is reported to possess psychostimulant, entactogenic and hallucinogenic effects. The purpose of this study was to examine the effects of acute administration of mephedrone on extracellular levels of dopamine (DA) and serotonin (5-HT) in the nucleus accumbens of awake rats and compare these effects to those induced by 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) and amphetamine. Microdialysis sampling was performed while simultaneously recording locomotor activity in rats and the monoamines were determined by HPLC with electrochemical detection. Mephedrone (3 mg.kg(-1) s.c.) and (+)-amphetamine (1 mg.kg(-1) s.c.) caused rapid increases in extracellular DA levels to 496% and 412%, respectively, whereas MDMA (3 mg.kg(-1) s.c.) showed only a moderate effect (235%). The corresponding 5-HT levels increased to 941% (mephedrone) and 911% (MDMA), but only to 165% following amphetamine. The calculated half-lives (t(1/2) ) for elimination rate of mephedrone, MDMA and amphetamine-induced increases in extracellular DA levels were 25, 303 and 51 min, the corresponding t(1/2) values for 5-HT were 26, 48 and 84 min, respectively. Locomotor activation was highest for amphetamine, whereas both mephedrone and MDMA showed about three times lower and short-lasting effects. Mephedrone resembles the neurochemical and functional properties of MDMA, but also shows amphetamine-like effect on rapid release and elimination of DA in the brain reward system, a feature that may contribute to its potent reinforcing properties.
Kehr J et al; Br J Pharmacol. 2011 May 26. doi: 10.1111/j.1476-5381.2011.01499.x. (Epub ahead of print)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Wiley References

14.5 Chemical Co-Occurrences in Literature

14.6 Chemical-Gene Co-Occurrences in Literature

14.7 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Drug-Drug Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 ChemIDplus

18.4 ChEMBL Target Tree

18.5 UN GHS Classification

18.6 Drug Enforcement Administration (DEA) Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 CCSBase Classification

18.9 EPA DSSTox Classification

18.10 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Mephedrone
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  11. ChEBI
  12. Drug Enforcement Administration (DEA)
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    https://www.justice.gov/legalpolicies
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  13. Open Targets
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    https://platform-docs.opentargets.org/licence
  14. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  15. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  17. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  18. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  19. Japan Chemical Substance Dictionary (Nikkaji)
  20. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  21. MassBank Europe
  22. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  23. Metabolomics Workbench
  24. SpectraBase
    4-METHYLMETHCATHINONE;2-(METHYLAMINO)-1-(4-METHYLPHENYL)-PROPAN-1-ONE;4-MMC
    https://spectrabase.com/spectrum/2gnpVdsw3EX
  25. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  26. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  27. Springer Nature
  28. Wikidata
  29. Wikipedia
  30. Wiley
  31. PubChem
  32. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  33. GHS Classification (UNECE)
  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
  36. NCBI
CONTENTS