Anpirtoline
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| drug_name =
| image = Anpirtoline.svg
| width = 225px
| caption =
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration =
| class = Serotonin receptor modulator Serotonin 5-HT1B receptor agonist
| ATC_prefix =
| ATC_suffix =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =
| CAS_number = 98330-05-3
| CAS_supplemental =
| PubChem = 65854
| PubChemSubstance =
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 59266
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 32K9S228IK
| KEGG =
| ChEBI = 92968
| ChEMBL = 1316374
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = D-16949; 6-Chloro-2-[piperidinyl-4-thio]pyridine
| IUPAC_name = 2-chloro-6-piperidin-4-ylsulfanylpyridine
| C=10 | H=13 | Cl=1 | N=2 | S=1
| SMILES = C1CNCCC1SC2=NC(=CC=C2)Cl
| StdInChI = 1S/C10H13ClN2S/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8/h1-3,8,12H,4-7H2
| StdInChIKey = GGALEXMXDMUMDM-UHFFFAOYSA-N
}}
Anpirtoline ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code name D-16949), also known as 2-chloro-6-piperidin-4-ylsulfanylpyridine, is a serotonin receptor modulator which was under development for the treatment of major depressive disorder (MDD) and pain but was never marketed.{{cite web | title=Anpirtoline | website=AdisInsight | date=8 February 2011 | url=https://adisinsight.springer.com/drugs/800000671 | access-date=24 February 2025}}{{cite journal | vauthors = Schlicker E, Werner U, Hamon M, Gozlan H, Nickel B, Szelenyi I, Göthert M | title = Anpirtoline, a novel, highly potent 5-HT1B receptor agonist with antinociceptive/antidepressant-like actions in rodents | journal = Br J Pharmacol | volume = 105 | issue = 3 | pages = 732–738 | date = March 1992 | pmid = 1628159 | pmc = 1908466 | doi = 10.1111/j.1476-5381.1992.tb09047.x | url = }}{{cite journal | vauthors = Göthert M, Hamon M, Barann M, Bönisch H, Gozlan H, Laguzzi R, Metzenauer P, Nickel B, Szelenyi I | title = 5-HT3 receptor antagonism by anpirtoline, a mixed 5-HT1 receptor agonist/5-HT3 receptor antagonist | journal = Br J Pharmacol | volume = 114 | issue = 2 | pages = 269–274 | date = January 1995 | pmid = 7881726 | pmc = 1510248 | doi = 10.1111/j.1476-5381.1995.tb13222.x | url = }}
It is a serotonin 5-HT1B and 5-HT1D receptor agonist, a serotonin 5-HT1A receptor ligand, a serotonin 5-HT3 receptor antagonist, and also binds to the serotonin 5-HT2 receptors with weak affinity. However, it acts preferentially as a serotonin 5-HT1B receptor agonist and is sometimes described as being selective in this action. It causes a decrease in serotonin synthesis and a reduction in aggressive behavior.
Anpirtoline is a synthetic compound. Anpirtoline hydrochloride appears as a white solid and is soluble in water. Being synthetic, the compound can be purchased from suppliers.
Properties
= Physical =
Anpirtoline hydrochloride appears as a white solid at room temperature and is soluble in water and DMSO. Its has a density of 1.27 g/cm3{{cite web|url=http://www.chem-info.com/trade/sell/Anpirtoline-hydrochloride-892253.html |title=Anpirtoline Hydrochloride |publisher=Chem-Info |accessdate=2012-10-19}} and a molar mass of 265.20. Structurally, the most notable parts of anpirtoline hydrochloride are two six-membered rings bonded via a sulfur atom.{{cite web|url=http://www.scbt.com/datasheet-201108-Anpirtoline-hydrochloride.html |title=Product Block - Chemicals - Serotonergics - Anpirtoline Hydrochloride |publisher=Santa Cruz Biotechnology, Inc. |accessdate=2012-10-19}}
= Chemical =
The melting point of anpirtoline hydrochloride is 126-128 °C. The flash point of the compound is 174 °C. Many of Anpirtoline hydrochloride's chemical properties remain unknown or untested.
Uses
Currently, anpirtoline is primarily used for research purposes due to its receptor agonist and receptor antagonist properties. Studies involving social instigation, aggression, and other behavioral traits make ample use of the compound.{{cite journal | vauthors = de Almeida RM, Miczek KA | title = Aggression escalated by social instigation or by discontinuation of reinforcement ("frustration") in mice: inhibition by anpirtoline: a 5-HT1B receptor agonist | journal = Neuropsychopharmacology | volume = 27 | issue = 2 | pages = 171–181 | date = August 2002 | pmid = 12093591 | doi = 10.1016/S0893-133X(02)00291-9 | s2cid = 24466803 | doi-access = free }}
Storage
Anpirtoline hydrochloride should be stored in a cool, well-ventilated area that is not exposed to direct sunlight.