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MedKoo Cat#: 581076 | Name: Anpirtoline hydrochloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anpirtoline HCl is highly potent 5-HT1B receptor agonist which decreases central serotonin synthesis and attenuates aggressive behavior in vivo. Anpirtoline HCl also acts as an antagonist at 5-HT3 receptors and is brain penetrant. Anpirtoline is a receptor agonist with antinociceptive/antidepressant-like actions in rodents.

Chemical Structure

Anpirtoline hydrochloride
Anpirtoline hydrochloride
CAS#99201-87-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 581076

Name: Anpirtoline hydrochloride

CAS#: 99201-87-3 (HCl)

Chemical Formula: C20H28Cl4N4S2

Exact Mass: 528.0509

Molecular Weight: 530.39

Elemental Analysis: C, 45.29; H, 5.32; Cl, 26.73; N, 10.56; S, 12.09

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 Weeks
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Related CAS #
99201-87-3 (HCl) 98330-05-3 (free base)
Synonym
Anpirtoline hydrochloride; D 16949; D16949;
IUPAC/Chemical Name
2-chloro-6-(piperidin-4-ylthio)pyridine hydrochloride
InChi Key
GRXDJABVNGUGCW-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H13ClN2S.ClH/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8;/h1-3,8,12H,4-7H2;1H
SMILES Code
Clc1cccc(SC2CCNCC2)n1.Cl
Appearance
Solid powder
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 530.39 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.

Recalculate based on batch purity %
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: 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. 3: 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. 4: Metzenauer P, Barnes NM, Costall B, Gozlan H, Hamon M, Kelly ME, Murphy DA, Naylor RJ. Anxiolytic-like actions of anpirtoline in a mouse light-dark aversion paradigm. Neuroreport. 1992 Jun;3(6):527-9. PubMed PMID: 1356500. 5: 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. 6: 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. 7: Rádl S, Hezký P, Proska J, Krejcí I. Analgetically active substances derived from structures of anpirtoline and epibatidine. Gen Physiol Biophys. 1998 Jun;17 Suppl 1:26-9. PubMed PMID: 9789748. 8: Chenu F, David DJ, Leroux-Nicollet I, Le Maître E, Gardier AM, Bourin M. Serotonin1B heteroreceptor activation induces an antidepressant-like effect in mice with an alteration of the serotonergic system. J Psychiatry Neurosci. 2008 Nov;33(6):541-50. PubMed PMID: 18982177; PubMed Central PMCID: PMC2575758. 9: Pérez Maceira JJ, Mancebo MJ, Aldegunde M. The involvement of 5-HT-like receptors in the regulation of food intake in rainbow trout (Oncorhynchus mykiss). Comp Biochem Physiol C Toxicol Pharmacol. 2014 Apr;161:1-6. doi: 10.1016/j.cbpc.2013.12.003. Epub 2013 Dec 21. PubMed PMID: 24365333. 10: Hillegaart V, Ahlenius S. Facilitation and inhibition of male rat ejaculatory behaviour by the respective 5-HT1A and 5-HT1B receptor agonists 8-OH-DPAT and anpirtoline, as evidenced by use of the corresponding new and selective receptor antagonists NAD-299 and NAS-181. Br J Pharmacol. 1998 Dec;125(8):1733-43. PubMed PMID: 9886765; PubMed Central PMCID: PMC1565750. 11: 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. 12: Rádl S, Kovárová L, Hezky P, Vosátka V, Königová O, Proska J, Krejcí I. Synthesis and analgesic activity of some condensed analogs of anpirtoline. Arch Pharm (Weinheim). 1999 Jun;332(6):208-12. PubMed PMID: 10399490. 13: Zhou W, Chen L, Paul J, Yang S, Li F, Sampson K, Woodgett JR, Beaulieu JM, Gamble KL, Li X. The effects of glycogen synthase kinase-3beta in serotonin neurons. PLoS One. 2012;7(8):e43262. doi: 10.1371/journal.pone.0043262. Epub 2012 Aug 17. PubMed PMID: 22912839; PubMed Central PMCID: PMC3422264. 14: Rádl S, Hezky P, Proska J, Krejcí I. Synthesis and analgesic activity of some quinazoline analogs of anpirtoline. Arch Pharm (Weinheim). 2000 Nov;333(11):381-6. PubMed PMID: 11129980. 15: Miczek KA, de Almeida RM. Oral drug self-administration in the home cage of mice: alcohol-heightened aggression and inhibition by the 5-HT1B agonist anpirtoline. Psychopharmacology (Berl). 2001 Oct;157(4):421-9. PubMed PMID: 11605102. 16: Engel J, Bork A, Nubert I, Schönenberger H. [Synthesis of 14C-anpirtoline]. Arch Pharm (Weinheim). 1988 Nov;321(11):821-2. German. PubMed PMID: 3219051. 17: Ahlander-Lüttgen M, Madjid N, Schött PA, Sandin J, Ogren SO. Analysis of the role of the 5-HT1B receptor in spatial and aversive learning in the rat. Neuropsychopharmacology. 2003 Sep;28(9):1642-55. Epub 2003 Jul 2. PubMed PMID: 12838273. 18: Rádl S, Hezky P, Proska J, Krejcí I. Synthesis and analgesic activity of some deaza derivatives of anpirtoline. Arch Pharm (Weinheim). 1999 Jan;332(1):13-8. PubMed PMID: 10073139. 19: O'Neill MF, Parameswaran T. RU24969-induced behavioural syndrome requires activation of both 5HT1A and 5HT1B receptors. Psychopharmacology (Berl). 1997 Aug;132(3):255-60. PubMed PMID: 9292625. 20: Rádl S, Hezky P, Proska J, Hejnová L, Krejcí I. Synthesis and analgesic activity of some side-chain modified anpirtoline derivatives. Arch Pharm (Weinheim). 2000 May;333(5):107-12. PubMed PMID: 10863793.