AD-1211

AD-1211

AD-1211 is an opioid analgesic drug invented in the 1970s by Dainippon 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 mixed agonist–antagonist at opioid receptors with a similar pharmacological profile to pentazocine,^[1] and has atypical opioid effects with little development of toleranceordependence seen after extended administration in animal studies.^[2]^[3]

AD-1211
Clinical data

Other names	AD-1211
ATC code	none
Identifiers
IUPAC name 1-(3-Methyl-2-butenyl)-4-[(1R)-1-phenyl-2-(3-hydroxyphenyl)ethyl]piperazine
CAS Number	83374-58-7^Y 61311-01-1 (R)-enantiomer
PubChem CID	173526
ChemSpider	26286944^Y
UNII	7YT87DVF55
CompTox Dashboard (EPA)	DTXSID00997906
Chemical and physical data
Formula	C₂₃H₃₀N₂O
Molar mass	350.506 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1c(O)cccc1CC(c3ccccc3)N(CC2)CCN2C\C=C(\C)/C
InChI 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^Y Key:WLHCNEPBQJOHKW-HSZRJFAPSA-N^Y
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References

^ 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.

^ 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.

^ 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.

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Last edited on 28 October 2023,

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