MESOCARB

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H18N4O2
Molecular Weight	322.3611
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CC1=CC=CC=C1)[N+]2=NOC([N-]C(=O)NC3=CC=CC=C3)=C2

InChI

InChIKey=OWFUPROYPKGHMH-UHFFFAOYSA-N

InChI=1S/C18H18N4O2/c1-14(12-15-8-4-2-5-9-15)22-13-17(24-21-22)20-18(23)19-16-10-6-3-7-11-16/h2-11,13-14H,12H2,1H3,(H-,19,20,21,23)

HIDE SMILES / InChI

Molecular Formula	C18H19N4O2
Molecular Weight	323.3691
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.rlsnet.ru/mnn_index_id_1188.htm | https://www.ncbi.nlm.nih.gov/pubmed/21300706 | https://www.ncbi.nlm.nih.gov/pubmed/7312716 | https://www.wada-ama.org/sites/default/files/resources/files/yli_kauhaluoma_2005.pdf

Mesocarb (sydnocarb or 3-(beta-phenylisopropyl)-N-phenylcarbamoylsydnonimine) is a psychomotor stimulant N-alkylated amphetamine derivative. Mesocarb is a selective inhibitor of dopamine uptake, it potently blocks dopamine transporter. It is very likely that mesocarb is being used by drug addicts. Mesocarb is included in the World Anti-Doping Agency’s list of substances and methods that are prohibited in sports. It is used in Russia for the treatment of a variety of neuropsychiatric comorbidities.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent dopamine transporter 42 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21300706	Inhibitor 8297		8.3 nM [Ki]

PubMed

Title	Date	PubMed
Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine.	1999 Mar	10027871
Characterization of pharmacological and wake-promoting properties of the dopaminergic stimulant sydnocarb in rats.	2011 May	21300706

Patents

Sample Use Guides

In Vivo Use Guide

The drug is administered orally, before meals, 1-2 times a day in the first half of the day. Adults: initial dose of 0.005 g / day; if necessary - up to 0,015-0,05 g / day; maintenance dose - 0.005-0.01 g / day, the highest single dose - 0.075 g, daily - 0.15 g

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:23:10 UTC 2023` Edited by `admin` on `Sat Dec 16 17:23:10 UTC 2023`
Record UNII	UMT8MP2NDU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MESOCARB

Official Name

English

SIDNOCARB

Common Name

English

MESOCARB [MART.]

Common Name

English

mesocarb [INN]

Common Name

English

Mesocarb [WHO-DD]

Common Name

English

SYDNONE IMINE, 3-(1-METHYL-2-PHENYLETHYL)-N-((PHENYLAMINO)CARBONYL)-

Systematic Name

English

1,2,3-OXADIAZOLIUM, 3-(1-METHYL-2-PHENYLETHYL)-5-(((PHENYLAMINO)CARBONYL)AMINO)-, INNER SALT

Systematic Name

English

SYDNOCARB

Common Name

English

MLR-1017

Code

English

SYDNONE IMINE, 3-(.ALPHA.-METHYLPHENETHYL)-N-(PHENYLCARBAMOYL)-

Systematic Name

English

DEA NO. 1227

Code

English

3-(.ALPHA.-METHYLPHENETHYL)-N-(PHENYLCARBAMOYL)SYDNONE IMINE

Systematic Name

English

N-phenyl-N ′-(3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium-5-yl)carbamimidate

Systematic Name

English

Classification Tree Code System Code

DEA NO.

1227