TAN-67

TAN-67

Identifiers
IUPAC name 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
PubChem (CID)	9950038
ChemSpider	8125649
KEGG	C20168
ChEMBL	CHEMBL327745
Chemical and physical data
Formula	C23H24N3O
Molar mass	344.449 g/mol
3D model (Jmol)	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 a opioid drug used in scientific research that acts as a potent and selective δ-opioid agonist,^[1] selective for the δ₁ subtype.^[2] It has analgesic properties^[3][4] and induces dopamine release in nucleus accumbens.^[5] It also protects both heart and brain tissue from hypoxic tissue damage through multiple mechanisms involving among others an interaction between δ receptors and mitochondrial K(ATP) channels.^{[6][7][8][9][10]}

References

1. Fujii H, Kawai K, Kawamura K, Mizusuna A, Onoda Y, Murachi M, Tanaka T, Endoh T, Nagase H. Synthesis of optically active TAN-67, a highly selective delta opioid receptor agonist, and investigation of its pharmacological properties. Drug Design and Discovery. 2001;17(4):325-30. PMID 11765135
2. Nagase H, Kawai K, Hayakawa J, Wakita H, Mizusuna A, Matsuura H, Tajima C, Takezawa Y, Endoh T. 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 and Pharmaceutical Bulletin (Tokyo). 1998 Nov;46(11):1695-702. PMID 9845952
3. Yajima Y, Narita M, Tsuda M, Imai S, Kamei J, Nagase H, Suzuki T. Modulation of NMDA- and (+)TAN-67-induced nociception by GABA(B) receptors in the mouse spinal cord. Life Sciences. 2000 Dec 29;68(6):719-25. PMID 11205886
4. Nagase H, Yajima Y, Fujii H, Kawamura K, Narita M, Kamei J, Suzuki T. The pharmacological profile of delta opioid receptor ligands, (+) and (-) TAN-67 on pain modulation. Life Sciences. 2001 Apr 6;68(19-20):2227-31. PMID 11358331
5. Fusa K, Takahashi I, Watanabe S, Aono Y, Ikeda H, Saigusa T, Nagase H, Suzuki T, Koshikawa N, Cools AR. 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. 2005;130(3):745-55. PMID 15590157
6. Fryer RM, Hsu AK, Nagase H, Gross GJ. Opioid-induced cardioprotection against myocardial infarction and arrhythmias: mitochondrial versus sarcolemmal ATP-sensitive potassium channels. Journal of Pharmacology and Experimental Therapeutics. 2000 Aug;294(2):451-7. PMID 10900218
7. Huh J, Gross GJ, Nagase H, Liang BT. 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. 2001 Jan;280(1):H377-83. PMID 11123254
8. Patel HH, Ludwig LM, Fryer RM, Hsu AK, Warltier DC, Gross GJ. Delta opioid agonists and volatile anesthetics facilitate cardioprotection via potentiation of K(ATP) channel opening. FASEB Journal. 2002 Sep;16(11):1468-70. PMID 12205051
9. Maslov LN, Platonov AA, Lasukova TV, Lishmanov IuB, Oeltgen P, Nagase H, Podoksenov IuK, Podoksenov AIu. 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. (Russian) 2006 Oct-Dec;(4):13-7. PMID 17300082
10. Tian XS, Zhou F, Yang R, Xia Y, Wu GC, Guo JC. Effects of intracerebroventricular injection of delta-opioid receptor agonist TAN-67 or antagonist naltrindole on acute cerebral ischemia in rat. Sheng Li Xue Bao (Chinese). 2008 Aug 25;60(4):475-484. PMID 18690389