Menabitan

Menabitan

Clinical data
ATC code	None
Legal status
Legal status	Equivalent of a Schedule I drug via the Federal Analogue Act
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	83784-21-8 58019-50-4 (HCl)
PubChem (CID)	189877
ChemSpider	164903
Chemical and physical data
Formula	C37H56N2O3
Molar mass	576.85214 g/mol
3D model (Jmol)	Interactive image
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

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]

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

• A-40174 (SP-1)
• Dimethylheptylpyran

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. Society for Experimental Biology and Medicine (New York, N.Y.). 154 (2): 228–31. doi:10.3181/00379727-154-39643. PMID 402656.
2. David J. Triggle (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.