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TAN-67

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Chemical compound

Pharmaceutical compound

TAN-67
Identifiers

IUPAC name rel-3-[(4aS,12aR)-2-Methyl-1,3,4,5,12,12a-hexahydropyrido[3,4-b]acridin-4a(2H)-yl]phenol
CAS Number	148545-09-9
PubChemCID	9950038
ChemSpider	8125649
UNII	UY7TB22PB7
KEGG	C20168
ChEMBL	ChEMBL327745
Chemical and physical data
Formula	C₂₃H₂₄N₂O
Molar mass	344.458 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CC[C@@]2(CC3=NC4=CC=CC=C4C=C3C[C@H]2C1)C5=CC(=CC=C5)O
InChI InChI=1S/C23H24N2O/c1-25-10-9-23(18-6-4-7-20(26)13-18)14-22-17(12-19(23)15-25)11-16-5-2-3-8-21(16)24-22/h2-8,11,13,19,26H,9-10,12,14-15H2,1H3/t19-,23+/m0/s1 Key:LEPBHAAYNPPRRA-WMZHIEFXSA-N
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TAN-67 (SB-205,607) is anopioid drug used inscientific research that acts as a potent and selectiveδ-opioid agonist,^[1] selective for the δ₁ subtype.^[2] It hasanalgesic properties^[3]^[4] and inducesdopamine release innucleus accumbens.^[5] It also protects both heart and brain tissue fromhypoxic tissue damage through multiple mechanisms involving among others an interaction between δ receptors andmitochondrial K(ATP) channels.^[6]^[7]^[8]^[9]^[10]

References

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^Fujii H, Kawai K, Kawamura K, Mizusuna A, Onoda Y, Murachi M, et al. (2001). "Synthesis of optically active TAN-67, a highly selective delta opioid receptor agonist, and investigation of its pharmacological properties".Drug Design and Discovery.17 (4):325–30.PMID 11765135.
^Nagase H, Kawai K, Hayakawa J, Wakita H, Mizusuna A, Matsuura H, et al. (November 1998)."Rational drug design and synthesis of a highly selective nonpeptide delta-opioid agonist, (4aS*,12aR*)-4a-(3-hydroxyphenyl)-2-methyl- 1,2,3,4,4a,5,12,12a-octahydropyrido[3,4-b]acridine (TAN-67)".Chemical & Pharmaceutical Bulletin.46 (11):1695–702.doi:10.1248/cpb.46.1695.PMID 9845952.
^Yajima Y, Narita M, Tsuda M, Imai S, Kamei J, Nagase H, Suzuki T (December 2000). "Modulation of NMDA- and (+)TAN-67-induced nociception by GABA(B) receptors in the mouse spinal cord".Life Sciences.68 (6):719–25.doi:10.1016/s0024-3205(00)00975-9.PMID 11205886.
^Nagase H, Yajima Y, Fujii H, Kawamura K, Narita M, Kamei J, Suzuki T (April 2001). "The pharmacological profile of delta opioid receptor ligands, (+) and (-) TAN-67 on pain modulation".Life Sciences.68 (19–20):2227–31.doi:10.1016/s0024-3205(01)01010-4.PMID 11358331.
^Fusa K, Takahashi I, Watanabe S, Aono Y, Ikeda H, Saigusa T, et al. (2005). "The non-peptidic delta opioid receptor agonist TAN-67 enhances dopamine efflux in the nucleus accumbens of freely moving rats via a mechanism that involves both glutamate and free radicals".Neuroscience.130 (3):745–55.doi:10.1016/j.neuroscience.2004.10.016.PMID 15590157.S2CID 42710264.
^Fryer RM, Hsu AK, Nagase H, Gross GJ (August 2000). "Opioid-induced cardioprotection against myocardial infarction and arrhythmias: mitochondrial versus sarcolemmal ATP-sensitive potassium channels".The Journal of Pharmacology and Experimental Therapeutics.294 (2):451–7.PMID 10900218.
^Huh J, Gross GJ, Nagase H, Liang BT (January 2001). "Protection of cardiac myocytes via delta(1)-opioid receptors, protein kinase C, and mitochondrial K(ATP) channels".American Journal of Physiology. Heart and Circulatory Physiology.280 (1): H377-83.doi:10.1152/ajpheart.2001.280.1.H377.PMID 11123254.S2CID 86775469.
^Patel HH, Ludwig LM, Fryer RM, Hsu AK, Warltier DC, Gross GJ (September 2002)."Delta opioid agonists and volatile anesthetics facilitate cardioprotection via potentiation of K(ATP) channel opening".FASEB Journal.16 (11):1468–70.doi:10.1096/fj.02-0170fje.PMID 12205051.S2CID 22952889.
^Maslov LN, Platonov AA, Lasukova TV, Lishmanov I, Oeltgen P, Nagase H, et al. (2006). "[Delta-opioid receptor activation prevents appearance of irreversible damages of cardiomyocytes and exacerbates myocardial contractility dysfunction during ischemia and reperfusion]".Patologicheskaia Fiziologiia I Eksperimental'naia Terapiia (4):13–7.PMID 17300082.
^Tian XS, Zhou F, Yang R, Xia Y, Wu GC, Guo JC (August 2008). "[Effects of intracerebroventricular injection of delta-opioid receptor agonist TAN-67 or antagonist naltrindole on acute cerebral ischemia in rat]".Sheng Li Xue Bao.60 (4):475–84.PMID 18690389.