Cyclazocine: Difference between revisions

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+{{Short description|Chemical compound}}
 {{Drugbox
 | Verifiedfields = changed
+| Watchedfields = changed
-| verifiedrevid = 399735209
+| verifiedrevid = 460109436
-| IUPAC_name = 3-(cyclopropylmethyl)-  6,11-dimethyl- 1,2,3,4,5,6-hexahydro- 2,6-methano- 3-benzazocin- 8-ol<br />or<br />2-cyclopropylmethyl- 2'-hydroxy- 5,9-dimethyl- 6,7-benzomorphan
+| IUPAC_name = 3-(Cyclopropylmethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol<br />or<br />2-Cyclopropylmethyl-2'-hydroxy-5,9-dimethyl-6,7-benzomorphan
-| image = Cyclazocine.png
+| image = Cyclazocine structure.svg
+| width = 200
 <!--Clinical data-->
 | tradename =
 | pregnancy_category =
-| legal_status = ?
+| legal_status =
 | routes_of_administration = Oral
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 <!--Identifiers-->
-| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number_Ref = {{cascite|changed|CAS}}
-| CAS_number = <!-- blanked - oldvalue: 7346-09-0 -->
+| CAS_number = 3572-80-3
 | ATC_prefix = none
 | ATC_suffix =
@@ Line 26: / Line 30: @@
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 18063
-| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII_Ref = {{fdacite|correct|FDA}}
-| UNII = J5W1B1159C
+| UNII =  J5W1B1159C
-| KEGG_Ref = {{keggcite|changed|kegg}}
+| KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = D03618
 | ChEMBL_Ref = {{ebicite|changed|EBI}}
-| ChEMBL = <!-- blanked - oldvalue: 279449 -->
+| ChEMBL = 56585
+<!--Chemical data-->
 | C=18 | H=25 | N=1 | O=1
-| molecular_weight = 271.40 g/mol
 | smiles = Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)C)C
-| InChI = 1/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3
-| InChIKey = YQYVFVRQLZMJKJ-UHFFFAOYAL
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3
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 }}
-'''Cyclazocine''' is a mixed [[opioid]] [[agonist]]/[[receptor antagonist|antagonist]] related to [[dezocine]], [[pentazocine]] and [[phenazocine]]. This family of opioid drugs is called the [[benzomorphan]]s or [[benzazocine]]s.<ref>{{cite journal |author=Sydney Archer, Stanley D Glick, Jean M Bidlack |title=Cyclazocine revisited - Neurochemical Research |year=1996 |volume=21 |issue=11 |pages=1369–1373 |doi=10.1007/BF02532378 |url=http://www.scribd.com/doc/43272398/Cyclazocine-revisited-Neurochemical-Research-1996-21-11-1369-1373-DOI-10-1007-BF02532378-http-dx-doi-org-10-1007-BF02532378}}</ref>
+'''Cyclazocine''' is a mixed [[opioid]] [[agonist]]/[[receptor antagonist|antagonist]] related to [[dezocine]], [[pentazocine]] and [[phenazocine]]. This family of opioid drugs is called the [[benzomorphan]]s or [[benzazocine]]s.<ref>{{cite journal | vauthors = Archer S, Glick SD, Bidlack JM | title = Cyclazocine revisited | journal = Neurochemical Research | volume = 21 | issue = 11 | pages = 1369–1373 | date = November 1996 | pmid = 8947927 | doi = 10.1007/BF02532378 | s2cid = 680860 }}</ref> It is a [[Kappa opioid receptor|KOR]] agonist and [[Mu opioid receptor|MOR]] [[partial agonist]], and also has high affinity for the [[Delta opioid receptor|DOR]].<ref name="pmid12065740">{{cite journal | vauthors = Bidlack JM, Cohen DJ, McLaughlin JP, Lou R, Ye Y, Wentland MP | title = 8-Carboxamidocyclazocine: a long-acting, novel benzomorphan | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 302 | issue = 1 | pages = 374–380 | date = July 2002 | pmid = 12065740 | doi = 10.1124/jpet.302.1.374 | s2cid = 15864569 }}</ref>
 == Use ==
 Research into the use of cyclazocine for the treatment of [[bipolar_disorder|bipolar]] patients with depression was undertaken by Fink and colleagues (1970). It showed that 8 out of 10 patients experienced moderate improvement.
-Research during the 1960s and 1970s into the possible use of cyclazocine for management of pain, and later for assisting treatment of narcotic addiction was severely hampered by the drug's psychotomimetic, dysphoric, and hallucinatory effects.<ref>{{cite web |url=http://jama.ama-assn.org/content/202/3/191.full.pdf |title=Cyclazocine and Methadone in Narcotic Addiction |author=Alfred M. Freedman, MD, Max Fink, MD, Robert Sharoff, MD, and Arthur Zaks, MD}}</ref>
+Research during the 1960s and 1970s into the possible use of cyclazocine for management of pain, and later for assisting treatment of narcotic addiction was severely hampered by the drug's psychotomimetic, dysphoric, and hallucinatory effects.<ref>{{cite journal | vauthors = Freedman AM, Fink M, Sharoff R, Zaks A | title = Cyclazocine and methadone in narcotic addiction | journal = JAMA | volume = 202 | issue = 3 | pages = 191–194 | date = October 1967 | pmid = 6072354 | doi = 10.1001/jama.1967.03130160065011 }}</ref> The [[dysphoria|dysphoric]]/[[anxiogenic|anxiety inducing]] effects of the drug correlate with increasing dosage and would likely reduce the risk of abuse in the same manner as other opioids which preferentially act on the [[kappa opioid receptor|KOR]] versus the [[delta opioid receptor|DOR]] and [[mu opioid receptor|MOR]], although the side-effect threshold is often lower than the lowest effective dose.
-== Dosage ==
-Dosages of 1–3 mg were administered in the tests.
 == See also ==
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 {{Analgesics}}
 {{Hallucinogens}}
+{{Opioid receptor modulators}}
+{{Sigma receptor modulators}}
 [[Category:Synthetic opioids]]
 [[Category:Phenols]]
 [[Category:Benzomorphans]]
-[[Category:Kappa agonists]]
+[[Category:Kappa-opioid receptor agonists]]
-[[sr:Ciklazocin]]