Menabitan

Menabitan (INN; SP-204), or menabitan hydrochloride (USAN), is a synthetic drug which acts as a potent cannabinoid receptor agonist.[1][2] It is closely related to natural cannabinoids of the tetrahydrocannabinol (THC) group, differing mainly by its longer and branched side chain, and the replacement of the 9-position carbon with a nitrogen.[1] It was studied as an analgesic in the 1970s and was found to possess antinociceptive effects in both humans and animals but was never marketed.[1][3][4]

Menabitan
Clinical data
ATC code
  • None
Legal status
Legal status
  • US: Analogue to a Schedule I/II drug (Schedule I)
Identifiers
IUPAC name
  • [5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H-chromeno[4,3-c]pyridin-10-yl] 2-methyl-4-(2-methylpiperidin-1-yl)butanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC37H56N2O3
Molar mass576.866 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC(C)C(C)C1=CC2=C(C3=C(CCN(C3)CC#C)C(O2)(C)C)C(=C1)OC(=O)C(C)CCN4CCCCC4C
InChI
  • InChI=1S/C37H56N2O3/c1-9-11-12-15-26(3)29(6)30-23-33(41-36(40)27(4)17-22-39-20-14-13-16-28(39)5)35-31-25-38(19-10-2)21-18-32(31)37(7,8)42-34(35)24-30/h2,23-24,26-29H,9,11-22,25H2,1,3-8H3
  • Key:ZWLPJYVIMWAEDC-UHFFFAOYSA-N

Due to its structural similarity to the schedule I/III drug THC it can be treated as a schedule I drug within the United States legal system under the Federal Analogue Act.

See also

References
  1. Green K, Kim K (February 1977). "Acute dose response of intraocular pressure to topical and oral cannabinoids". Proceedings of the Society for Experimental Biology and Medicine. 154 (2): 228–31. doi:10.3181/00379727-154-39643. PMID 402656. S2CID 32785623.
  2. Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 1271. ISBN 978-0-412-46630-4.
  3. Reggio PH (1987). "Molecular determinants for cannabinoid activity: refinement of a molecular reactivity template". NIDA Research Monograph. 79: 82–95. PMID 2830539.
  4. Gabriel G. Nahas (5 April 1999). Marihuana and Medicine. Humana Press. p. 46. ISBN 978-0-89603-593-5. Retrieved 9 May 2012.


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