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Anpirtoline

From Wikipedia, the free encyclopedia

Pharmaceutical compound
Anpirtoline
Clinical data
Other namesD-16949; 6-Chloro-2-[piperidinyl-4-thio]pyridine
Drug classSerotonin receptormodulatorSerotonin5-HT1B receptoragonist
Identifiers
  • 2-chloro-6-piperidin-4-ylsulfanylpyridine
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H13ClN2S
Molar mass228.74 g·mol−1
3D model (JSmol)
  • C1CNCCC1SC2=NC(=CC=C2)Cl
  • InChI=1S/C10H13ClN2S/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8/h1-3,8,12H,4-7H2
  • Key:GGALEXMXDMUMDM-UHFFFAOYSA-N

Anpirtoline (INNTooltip International Nonproprietary Name; developmental code nameD-16949), also known as2-chloro-6-piperidin-4-ylsulfanylpyridine, is aserotonin receptormodulator which was under development for the treatment ofmajor depressive disorder (MDD) andpain but was never marketed.[1][2][3]

It is aserotonin5-HT1B and5-HT1D receptoragonist, a serotonin5-HT1A receptorligand, a serotonin5-HT3 receptorantagonist, and also binds to the serotonin5-HT2 receptors with weakaffinity.[2][3] However, it acts preferentially as a serotonin 5-HT1B receptor agonist and is sometimes described as beingselective in this action.[2] It causes a decrease inserotonin synthesis and a reduction inaggressive behavior.

Anpirtoline is asyntheticcompound. Anpirtoline hydrochloride appears as a white solid and is soluble in water. Being synthetic, the compound can be purchased from suppliers.

Properties

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Physical

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Anpirtoline hydrochloride appears as a white solid at room temperature and issoluble in water andDMSO. Its has a density of 1.27 g/cm3[4] and a molar mass of 265.20. Structurally, the most notable parts of anpirtoline hydrochloride are two six-membered rings bonded via asulfur atom.[5]

Chemical

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Themelting point of anpirtoline hydrochloride is 126-128 °C. Theflash point of the compound is 174 °C. Many of Anpirtoline hydrochloride'schemical properties remain unknown or untested.[5]

Uses

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Currently, anpirtoline is primarily used for research purposes due to itsreceptor agonist andreceptor antagonist properties. Studies involving social instigation,aggression, and other behavioral traits make ample use of thecompound.[6]

Storage

[edit]

Anpirtoline hydrochloride should be stored in a cool, well-ventilated area that is not exposed to direct sunlight.

References

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  1. ^"Anpirtoline".AdisInsight. 8 February 2011. Retrieved24 February 2025.
  2. ^abcSchlicker E, Werner U, Hamon M, Gozlan H, Nickel B, Szelenyi I, et al. (March 1992)."Anpirtoline, a novel, highly potent 5-HT1B receptor agonist with antinociceptive/antidepressant-like actions in rodents".Br J Pharmacol.105 (3):732–738.doi:10.1111/j.1476-5381.1992.tb09047.x.PMC 1908466.PMID 1628159.
  3. ^abGöthert M, Hamon M, Barann M, Bönisch H, Gozlan H, Laguzzi R, et al. (January 1995)."5-HT3 receptor antagonism by anpirtoline, a mixed 5-HT1 receptor agonist/5-HT3 receptor antagonist".Br J Pharmacol.114 (2):269–274.doi:10.1111/j.1476-5381.1995.tb13222.x.PMC 1510248.PMID 7881726.
  4. ^"Anpirtoline Hydrochloride". Chem-Info. Retrieved2012-10-19.
  5. ^ab"Product Block - Chemicals - Serotonergics - Anpirtoline Hydrochloride". Santa Cruz Biotechnology, Inc. Retrieved2012-10-19.
  6. ^de Almeida RM, Miczek KA (August 2002)."Aggression escalated by social instigation or by discontinuation of reinforcement ("frustration") in mice: inhibition by anpirtoline: a 5-HT1B receptor agonist".Neuropsychopharmacology.27 (2):171–181.doi:10.1016/S0893-133X(02)00291-9.PMID 12093591.S2CID 24466803.
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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