Menabitan

Menabitan
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • [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)
  • 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=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

Menabitan (INN: SP-204) is a synthetic drug which acts as a potent cannabinoid receptor agonist. 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. It is a structural analog of nabitan and dimethylheptylpyran. It was studied as an analgesic in the 1970s and was found to possess analgesic effects in both humans and animals but was never marketed.

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. 1 2 3 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.