Anazocine

Anazocine (INN; also known as azabicyclane or CS-307) is an opioid analgesic of the morphan/benzomorphan family developed in the middle 1960s in the United States which was never marketed.^[1][2] It is listed by some sources as a teratogen.^[3]

Anazocine

Clinical data
ATC code	None
Identifiers
IUPAC name 9-Methoxy-3-methyl-9-phenyl-3-azabicyclo[3.3.1]nonane
CAS Number	15378-99-1 21650-02-2 (citrate)
PubChem CID	27213
ChemSpider	25327
UNII	K2S5VMM2SG
ChEMBL	ChEMBL2105792
CompTox Dashboard (EPA)	DTXSID30864591
Chemical and physical data
Formula	C16H23NO
Molar mass	245.366 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(C2(c1ccccc1)C3CCCC2CN(C3)C)C
InChI InChI=1S/C16H23NO/c1-17-11-14-9-6-10-15(12-17)16(14,18-2)13-7-4-3-5-8-13/h3-5,7-8,14-15H,6,9-12H2,1-2H3 Key:YFFNPIAPUDUYAU-UHFFFAOYSA-N

The structure and properties of several related α- and β-azabicyclane opioids was explored.^[4] Anazocine's chemical and structural relatives include opioid partial agonists, mixed agonist-antagonists, pure agonists, antagonists, and atypical non-opioid analgesics. It was tested in pigeons and in other experiments which contrasted and compared its analgesic effects to those of the phenazepine opioid ethoheptazine and the phenalkoxam open chain opioid propoxyphene,^[5] and pethidine as well.^[6]

See also

• Benzomorphan

References

1. Macdonald F (1997). Ganellin CR, Triggle DJ (eds.). Dictionary of Pharmacological Agents. CRC Press. p. 146. ISBN 978-0-412-46630-4. Retrieved 22 April 2012.
2. Kobayashi S, Hasegawa K, Oshima T, Takagi H (September 1970). "The pharmacology of azabicyclane, a new analgesic agent". Toxicology and Applied Pharmacology. 17 (2): 344–354. doi:10.1016/0041-008X(70)90191-2. PMID 5528556.
3. "Teratogens". Radiological and Environmental Management. Purdue University. Archived from the original on 2016-02-15. Retrieved 2016-03-01.
4. Froimowitz M, Salva P, Hite GJ, Gianutsos G, Suzdak P, Heyman R (1984). "Conformational properties of α- and β-azabicyclane opiates. The effect of conformation on pharmacological activity". Journal of Computational Chemistry. 5 (4): 291–298. doi:10.1002/jcc.540050403. S2CID 97334125.
5. Kobayashi S, Hasegawa K, Oshima T, Takagi H (September 1970). "The pharmacology of azabicyclane, a new analgesic agent". Toxicology and Applied Pharmacology. 17 (2): 344–354. doi:10.1016/0041-008X(70)90191-2. PMID 5528556.
6. Leander JD (1979). "Effects of propoxyphene, ethoheptazine, and azabicyclane on schedule-controlled responding: attenuation by pentobarbital but not naloxone". Psychopharmacology. 66 (1): 19–22. doi:10.1007/BF00431983. PMID 44372. S2CID 29627833.