{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = 9-Methoxy-3-methyl-9-phenyl-3-azabicyclo[3.3.1]nonane | image = Anazocine structure.svg | image_class = skin-invert-image | CAS_number = 15378-99-1 | CAS_supplemental = <br />21650-02-2 (citrate) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = K2S5VMM2SG | ATC_prefix = None | ATC_suffix = | PubChem = 27213 | ChemSpiderID = 25327 | ChEMBL = 2105792 | C = 16 | H = 23 | N = 1 | O = 1 | smiles = O(C2(c1ccccc1)C3CCCC2CN(C3)C)C | StdInChI = 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 | StdInChIKey = YFFNPIAPUDUYAU-UHFFFAOYSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | legal_status = | routes_of_administration = }}
'''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.<ref name="Macdonald1997">{{cite book | vauthors = Macdonald F | veditors = Ganellin CR, Triggle DJ | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA146 | access-date = 22 April 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 146}}</ref><ref name="pmid5528556">{{cite journal | vauthors = Kobayashi S, Hasegawa K, Oshima T, Takagi H | title = The pharmacology of azabicyclane, a new analgesic agent | journal = Toxicology and Applied Pharmacology | volume = 17 | issue = 2 | pages = 344–354 | date = September 1970 | pmid = 5528556 | doi = 10.1016/0041-008X(70)90191-2 }}</ref> It is listed by some sources as a teratogen.<ref>{{Cite web |url=https://www.purdue.edu/ehps/rem/ih/terat.htm | title = Teratogens | work = Radiological and Environmental Management | publisher = Purdue University |access-date=2016-03-01 |archive-url=https://web.archive.org/web/20160215025937/https://www.purdue.edu/ehps/rem/ih/terat.htm |archive-date=2016-02-15 |url-status=dead }}</ref>
The structure and properties of several related α- and β-azabicyclane opioids was explored.<ref>{{cite journal | doi=10.1002/jcc.540050403 | volume=5 | issue=4 | title=Conformational properties of α- and β-azabicyclane opiates. The effect of conformation on pharmacological activity | journal=Journal of Computational Chemistry | pages=291–298| year=1984 | vauthors = Froimowitz M, Salva P, Hite GJ, Gianutsos G, Suzdak P, Heyman R | s2cid=97334125 }}</ref> 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,<ref>{{cite journal | vauthors = Kobayashi S, Hasegawa K, Oshima T, Takagi H | title = The pharmacology of azabicyclane, a new analgesic agent | journal = Toxicology and Applied Pharmacology | volume = 17 | issue = 2 | pages = 344–354 | date = September 1970 | pmid = 5528556 | doi = 10.1016/0041-008X(70)90191-2 }}</ref> and pethidine as well.<ref>{{cite journal | vauthors = Leander JD | title = Effects of propoxyphene, ethoheptazine, and azabicyclane on schedule-controlled responding: attenuation by pentobarbital but not naloxone | journal = Psychopharmacology | volume = 66 | issue = 1 | pages = 19–22 | year = 1979 | pmid = 44372 | doi = 10.1007/BF00431983 | s2cid = 29627833 }}</ref>
== See also == * Benzomorphan * P-7521
== References == {{Reflist|2}}
{{Analgesics}} {{Opioidergics}}
Category:Opioids