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 tolerance or dependence 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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See also

• Diphenidine
• Diphenpipenol
• Ephenidine
• Fluorolintane
• Lanicemine
• Lefetamine
• Methoxphenidine (MXP)
• MT-45
• Remacemide
• AH-7921