TAN-67

drugbox


IUPAC_name = 3- [(4aS,12aR)-11-amino-2-methyl-1,3,4,5,12,12a-hexahydropyrido [3,4-b] acridin-4a-yl] phenol
PubChem = 9798940
C = 23 | H = 25 | N = 3 | O = 1
molecular_weight = 359.464 g/mol
smiles = CN1CC [C@@] 2(CC3=NC4=CC=CC=C4C(=C3C [C@H] 2C1)N)C5=CC(=CC=C5)O
CAS_number = 148545-09-9
legal_status =

TAN-67 (SB-205,607) is a drug which is used in scientific research, which is a potent and selective δ-opioid agonist, [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] selective for the δ₁ subtype. [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] It has analgesic properties [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] [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] and induces dopamine release in the brain. [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] It also protects both heart and brain tissue from hypoxic tissue damage through multiple mechanisms involving amongst others an interaction between δ receptors and mitochondrial K(ATP) channels. [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] [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] [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] [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] [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]

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