Synonym
RTI 336; RTI336; RTI-336;
IUPAC/Chemical Name
5-((1R,2S,3S,5S)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl)-3-(p-tolyl)isoxazole hydrochloride
InChi Key
IZMZEMAKFSYLMD-SXBQIKTFSA-N
InChi Code
InChI=1S/C24H25ClN2O.ClH/c1-15-3-5-17(6-4-15)21-14-23(28-26-21)24-20(16-7-9-18(25)10-8-16)13-19-11-12-22(24)27(19)2;/h3-10,14,19-20,22,24H,11-13H2,1-2H3;1H/t19-,20+,22+,24-;/m0./s1
SMILES Code
CC1=CC=C(C2=NOC([C@@H]3[C@@](N4C)([H])CC[C@@]4([H])C[C@@H]3C5=CC=C(Cl)C=C5)=C2)C=C1.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
429.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Andersen ML, Sawyer EK, Carroll FI, Howell LL. Influence of chronic dopamine transporter inhibition by RTI-336 on motor behavior, sleep, and hormone levels in rhesus monkeys. Exp Clin Psychopharmacol. 2012 Apr;20(2):77-83. doi: 10.1037/a0026034. Epub 2011 Oct 24. PubMed PMID: 22023668; PubMed Central PMCID: PMC3302935.
2: Czoty PW, Martelle JL, Carroll FI, Nader MA. Lower reinforcing strength of the phenyltropane cocaine analogs RTI-336 and RTI-177 compared to cocaine in nonhuman primates. Pharmacol Biochem Behav. 2010 Sep;96(3):274-8. doi: 10.1016/j.pbb.2010.05.017. Epub 2010 May 24. PubMed PMID: 20580733; PubMed Central PMCID: PMC2907452.
3: Hiranita T, Wilkinson DS, Hong WC, Zou MF, Kopajtic TA, Soto PL, Lupica CR, Newman AH, Katz JL. 2-isoxazol-3-phenyltropane derivatives of cocaine: molecular and atypical system effects at the dopamine transporter. J Pharmacol Exp Ther. 2014 May;349(2):297-309. doi: 10.1124/jpet.113.212738. Epub 2014 Feb 11. Erratum in: J Pharmacol Exp Ther. 2014 Jun 1;349(3):534. PubMed PMID: 24518035; PubMed Central PMCID: PMC3989806.
4: Haile CN, Zhang XY, Carroll FI, Kosten TA. Cocaine self-administration and locomotor activity are altered in Lewis and F344 inbred rats by RTI 336, a 3-phenyltropane analog that binds to the dopamine transporter. Brain Res. 2005 Sep 7;1055(1-2):186-95. PubMed PMID: 16095575.
5: Carroll FI, Howard JL, Howell LL, Fox BS, Kuhar MJ. Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse. AAPS J. 2006 Mar 24;8(1):E196-203. Review. PubMed PMID: 16584128; PubMed Central PMCID: PMC2751440.
6: Carroll FI, Kosten TR, Buda JJ, Wang L, Walters BB. A Double-Blind, Placebo-Controlled Trial Demonstrating the Safety, Tolerability, and Pharmacokinetics of Single, Escalating Oral Doses of RTI-336. Front Pharmacol. 2018 Jul 10;9:712. doi: 10.3389/fphar.2018.00712. eCollection 2018. PubMed PMID: 30042675; PubMed Central PMCID: PMC6048956.
7: Howell LL, Carroll FI, Votaw JR, Goodman MM, Kimmel HL. Effects of combined dopamine and serotonin transporter inhibitors on cocaine self-administration in rhesus monkeys. J Pharmacol Exp Ther. 2007 Feb;320(2):757-65. Epub 2006 Nov 14. PubMed PMID: 17105829.
8: Carroll FI, Fox BS, Kuhar MJ, Howard JL, Pollard GT, Schenk S. Effects of dopamine transporter selective 3-phenyltropane analogs on locomotor activity, drug discrimination, and cocaine self-administration after oral administration. Eur J Pharmacol. 2006 Dec 28;553(1-3):149-56. Epub 2006 Sep 23. PubMed PMID: 17067572.