Synonym
Anpirtoline free base, Anpirtolina, Anpirtolinum, D-16949
IUPAC/Chemical Name
4-((6-Chloro-2-pyridyl)thio)piperidine
InChi Key
GGALEXMXDMUMDM-UHFFFAOYSA-N
InChi Code
1S/C10H13ClN2S/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8/h1-3,8,12H,4-7H2
SMILES Code
c1(Cl)nc(SC2CCNCC2)ccc1
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
228.74
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: Bézard E, Muñoz A, Tronci E, Pioli EY, Li Q, Porras G, Björklund A, Carta M. Anti-dyskinetic effect of anpirtoline in animal models of L-DOPA-induced dyskinesia. Neurosci Res. 2013 Dec;77(4):242-6. doi: 10.1016/j.neures.2013.10.002. Epub 2013 Oct 14. PubMed PMID: 24135129.
2: Watanabe A, Nakai A, Tohyama Y, Nguyen KQ, Diksic M. Effects of anpirtoline on regional serotonin synthesis in the rat brain: an autoradiographic study. Nucl Med Biol. 2006 Apr;33(3):325-32. Epub 2006 Mar 9. PubMed PMID: 16631081.
3: de Almeida RM, Miczek KA. Aggression escalated by social instigation or by discontinuation of reinforcement ("frustration") in mice: inhibition by anpirtoline: a 5-HT1B receptor agonist. Neuropsychopharmacology. 2002 Aug;27(2):171-81. PubMed PMID: 12093591.
4: Rilke O, Will K, Jähkel M, Oehler J. Behavioral and neurochemical effects of anpirtoline and citalopram in isolated and group housed mice. Prog Neuropsychopharmacol Biol Psychiatry. 2001 Jul;25(5):1125-44. PubMed PMID: 11444681.
5: Göthert M, Hamon M, Barann M, Bönisch H, Gozlan H, Laguzzi R, Metzenauer P, Nickel B, Szelenyi I. 5-HT3 receptor antagonism by anpirtoline, a mixed 5-HT1 receptor agonist/5-HT3 receptor antagonist. Br J Pharmacol. 1995 Jan;114(2):269-74. PubMed PMID: 7881726; PubMed Central PMCID: PMC1510248.
6: Hummel T, Hummel C, Friedel I, Pauli E, Kobal G. A comparison of the antinociceptive effects of imipramine, tramadol and anpirtoline. Br J Clin Pharmacol. 1994 Apr;37(4):325-33. PubMed PMID: 8018453; PubMed Central PMCID: PMC1364732.
7: Swedberg MD, Shannon HE, Nickel B, Goldberg SR. D-16949 (anpirtoline): a novel serotonergic (5-HT1B) psychotherapeutic agent assessed by its discriminative effects in the rat. J Pharmacol Exp Ther. 1992 Dec;263(3):1015-22. PubMed PMID: 1335050.
8: Schlicker E, Werner U, Hamon M, Gozlan H, Nickel B, Szelenyi I, Göthert M. Anpirtoline, a novel, highly potent 5-HT1B receptor agonist with antinociceptive/antidepressant-like actions in rodents. Br J Pharmacol. 1992 Mar;105(3):732-8. PubMed PMID: 1628159; PubMed Central PMCID: PMC1908466.
