Metazocine: Difference between revisions
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(2R,6R,11R) according to Opioid Analgesics By A.F. Casy, R.T. Parfitt Page 204. |
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| verifiedrevid = 462249359 |
| verifiedrevid = 462249359 |
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| IUPAC_name = (2R,6R,11R)-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-ol |
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| IUPAC_name = 1,2,3,4,5,6-hexahydro-3,6,11-trimethyl-2,6-methano-3-benzazocin-8-ol<Br />or<br />2'-hydroxy-2,5,9-trimethyl-6,7-benzomorphan |
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| image = Metazocine.png |
| image = Metazocine.png |
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| C=15 | H=21 | N=1 | O=1 |
| C=15 | H=21 | N=1 | O=1 |
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| molecular_weight = 231.333 g/mol |
| molecular_weight = 231.333 g/mol |
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| smiles = OC1=CC([C@@](C)([C@@]2([H])C)CCN(C)[C |
| smiles = OC1=CC([C@@](C)([C@@]2([H])C)CCN(C)[C@]2([H])C3)=C3C=C1 |
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| InChI = 1/C15H21NO/c1-10-14-8-11-4-5-12(17)9-13(11)15(10,2)6-7-16(14)3/h4-5,9-10,14,17H,6-8H2,1-3H3 |
| InChI = 1/C15H21NO/c1-10-14-8-11-4-5-12(17)9-13(11)15(10,2)6-7-16(14)3/h4-5,9-10,14,17H,6-8H2,1-3H3 |
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| InChIKey = YGSVZRIZCHZUHB-UHFFFAOYAZ |
| InChIKey = YGSVZRIZCHZUHB-UHFFFAOYAZ |
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Revision as of 15:58, 23 September 2012
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| Clinical data | |
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| Routes of administration | ? |
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| ECHA InfoCard | 100.020.998 |
| Chemical and physical data | |
| Formula | C15H21NO |
| Molar mass | 231.333 g/mol g·mol−1 |
| 3D model (JSmol) | |
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Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects,[1] mediated through a mixed agonist-antagonist action[2] at the mu opioid receptor,[3] its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors[4] and sigma receptors.[5][6]
See also
References
- ^ Hori M, Ban M, Imai E, Iwata N, Suzuki Y, Baba Y, Morita T, Fujimura H, Nozaki M, Niwa M. Novel nonnarcotic analgesics with an improved therapeutic ratio. Structure-activity relationships of 8-(methylthio)- and 8-(acylthio)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines. Journal of Medicinal Chemistry. 1985 Nov;28(11):1656-61.
- ^ Berzetei-Gurske I, Loew GH. The novel antagonist profile of (-)metazocine. Progress in Clinical and Biological Research. 1990;328:33-6.
- ^ Gharagozlou P, Demirci H, David Clark J, Lameh J. Activity of opioid ligands in cells expressing cloned mu opioid receptors. BMC Pharmacology. 2003 Jan 4;3:1.
- ^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J. Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacology. 2006 Jan 25;6:3.
- ^ Shannon HE. Pharmacological analysis of the phencyclidine-like discriminative stimulus properties of narcotic derivatives in rats. Journal of Pharmacology and Experimental Therapeutics. 1982 Jul;222(1):146-51.
- ^ Slifer BL, Balster RL, May EL. Reinforcing and phencyclidine-like stimulus properties of enantiomers of metazocine. Pharmacology, Biochemistry and Behaviour. 1986 Oct;25(4):785-9.