MT-45
From Wikipedia, the free encyclopedia
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|---|---|
| Systematic (IUPAC) name | |
| 1-cyclohexyl-4-(1,2-diphenylethyl)piperazine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 41537-67-1  52694-55-0 (S) enantiomer |
| ATC code | None |
| PubChem | CID 431865 |
| Synonyms | MT-45, IC-6 |
| Chemical data | |
| Formula | C24H32N2 |
| Mol. mass | 348.523 g/mol |
| SMILES | eMolecules & PubChem |
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MT-45 (IC-6) is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co.[1] It is chemically a 1-substituted-4-(1,2-diphenylethyl)piperazine derivative, which is structurally unrelated to most other opioid drugs. Racemic MT-45 has around the same potency as morphine, with almost all analgesic activity residing in the (S) enantiomer (interestingly the opposite stereochemistry from the related drug lefetamine).[2][3] It has been used as a lead compound from which a large family of potent opioid drugs[4] have been developed, including full agonists, partial agonists and antagonists at the three main opioid receptor subtypes.[5][6][7][8][9][10]
[edit] See also
[edit] References
- ^ US patent 3957788, Haruki Nishimura, Hitoshi Uno, Kagayaki Natsuka, Noriaki Shimokawa, Masanao Shimizu, Hideo Nakamura, "1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives and their salts", published 1975-15-01, issued 1976-18-05
- ^ Natsuka K, Nakamura H, Uno H, Umemoto S (December 1975). "Studies on 1-substituted 4-(1,2-diphenylethyl)piperazine derivatives and their analgesic activities. 1". Journal of Medicinal Chemistry 18 (12): 1240–4. doi:10.1021/jm00246a014. PMID 1195277.
- ^ Nakamura H, Shimizu M (May 1976). "Comparative study of 1-cyclohexyl-4-(1,2-diphenylethyl)-piperazine and its enantiomorphs on analgesic and othe pharmacological activities in experimental animals". Archives Internationales De Pharmacodynamie Et De Thérapie 221 (1): 105–21. PMID 962421.
- ^ US Patent 4080453
- ^ Natsuka K, Nakamura H, Negoro T, Uno H, Nishimura H (December 1978). "Studies on 1-substituted 4-(1,2-diphenylethyl)piperazine derivatives and their analgesic activities. 2. Structure-activity relationships of 1-cycloalkyl-4-(1,2-diphenylethyl)piperazines". Journal of Medicinal Chemistry 21 (12): 1265–9. doi:10.1021/jm00210a017. PMID 722735.
- ^ Shimokawa N, Nakamura H, Shimakawa K, Minami H, Nishimura H (January 1979). "Studies on analgesic agents. 1.1a Preparation of 1,2-diphenyl-2-(4-substituted 1-piperazinyl)ethanol derivatives and structure-activity relationships". Journal of Medicinal Chemistry 22 (1): 58–63. doi:10.1021/jm00187a014. PMID 106119.
- ^ Nakamura H, Ishii D, Yokoyama Y, Motoyoshi S, Natsuka K, Shimizu M (September 1980). "Analgesic and other pharmacological activities of a new narcotic antagonist analgesic (-)-1-(3-methyl-2-butenyl)-4-[2-(3-hydroxyphenyl)-1-phenylethyl]-piperazine and its enantiomorph in experimental animals". The Journal of Pharmacy and Pharmacology 32 (9): 635–42. PMID 6107365.
- ^ Nozaki M, Niwa M, Imai E, Hori M, Fujimura H (1983). "(1,2-Diphenylethyl) piperazines as potent opiate-like analgesics; the unusual relationships between stereoselectivity and affinity to opioid receptor". Life Sciences 33 Suppl 1: 431–4. PMID 6319898.
- ^ Natsuka K, Nakamura H, Nishikawa Y, Negoro T, Uno H, Nishimura H (October 1987). "Synthesis and structure-activity relationships of 1-substituted 4-(1,2-diphenylethyl)piperazine derivatives having narcotic agonist and antagonist activity". Journal of Medicinal Chemistry 30 (10): 1779–87. doi:10.1021/jm00393a017. PMID 3656354.
- ^ Natsuka K, Nishikawa Y, Nakamura H (December 1999). "Roles of two basic nitrogen atoms in 1-substituted 4-(1,2-diphenylethyl)piperazine derivatives in production of opioid agonist and antagonist activities". Chemical & Pharmaceutical Bulletin 47 (12): 1790–3. PMID 10748722.
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