AD-1211

AD-1211

Systematic (IUPAC) name
1-(3-methyl-2-butenyl)-4-[(1R)-1-phenyl-2-(3-hydroxyphenyl)ethyl]piperazine
Identifiers
CAS Number	83374-58-7 61311-01-1 (R) enantiomer
ATC code	none
PubChem	CID 173526
ChemSpider	26286944
Synonyms	AD-1211
Chemical data
Formula	C23H30N2O
Molar mass	350.496 g/mol
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 Key:WLHCNEPBQJOHKW-HSZRJFAPSA-N
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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]

See also

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

• AH-7921

References

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.
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.