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AD-1211

From Wikipedia, the free encyclopedia
Opioid analgesic drug
Pharmaceutical compound
AD-1211
Clinical data
Other namesAD-1211
ATC code
  • none
Identifiers
  • 1-(3-Methyl-2-butenyl)-4-[(1R)-1-phenyl-2-(3-hydroxyphenyl)ethyl]piperazine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H30N2O
Molar mass350.506 g·mol−1
3D model (JSmol)
  • c1c(O)cccc1CC(c3ccccc3)N(CC2)CCN2C\C=C(\C)/C
  • InChI=1S/C23H30N2O/c1-19(2)11-12-24-13-15-25(16-14-24)23(21-8-4-3-5-9-21)18-20-7-6-10-22(26)17-20/h3-11,17,23,26H,12-16,18H2,1-2H3/t23-/m1/s1 checkY
  • Key:WLHCNEPBQJOHKW-HSZRJFAPSA-N checkY
  (verify)

AD-1211 is anopioidanalgesic drug invented in the 1970s byDainippon Pharmaceutical Co. It is chemically a 1-substituted-4-prenyl-piperazine derivative, which is structurally unrelated to most other opioid drugs. The (S)-enantiomers in this series are more active as opioid agonists, but the less active (R)-enantiomer of this compound, AD-1211, is a mixedagonist–antagonist at opioid receptors with a similar pharmacological profile topentazocine,[1] and has atypical opioid effects with little development oftolerance ordependence seen after extended administration in animal studies.[2][3]

See also

[edit]

References

[edit]
  1. ^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.
  2. ^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.doi:10.1111/j.2042-7158.1980.tb13020.x.PMID 6107365.S2CID 27764413.
  3. ^Nakamura H, Ishii K, Yokoyama Y, Imazu C, Shimoda A, Kadokawa T, Shimizu M (November 1984). "Central actions of AD-1211, an analgesic lacking common opiate features".European Journal of Pharmacology.106 (2):345–56.doi:10.1016/0014-2999(84)90722-2.PMID 6529980.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
Phenylpiperazines
Benzylpiperazines
Naphthylpiperazines
Quinolinylpiperazines
Diphenylalkylpiperazines
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolylpiperazines
Tricyclic-linked piperazines
Others/uncategorized


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