Anpirtoline

Anpirtoline (chemical formula C10H13ClN2S) is a synthetic chemical compound used as a 5-HT1B receptor agonist as well as a 5-HT3 receptor antagonist, causing a decrease in serotonin synthesis and a reduction in aggressive behavior. Anpirtoline hydrochloride appears as a white solid and is soluble in water. Being synthetic, the compound can be purchased from suppliers.

Anpirtoline
Names
IUPAC name
2-Chloro-6-piperidin-4-ylsulfanylpyridine
Other names
6-Chloro-2-[piperidinyl-4-thio]pyridine
Identifiers
3D model (JSmol)
UNII
  • 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
  • C1CNCCC1SC2=NC(=CC=C2)Cl
Properties
C10H13ClN2S
Molar mass 228.74 g·mol−1
Appearance White solid
Density 1.27 g/cm3
Melting point 126–128 °C (259–262 °F; 399–401 K) (HCl)
25 mg/ml (HCl)
Solubility in DMSO 100 mM (HCl)
Hazards
Flash point 174 °C (345 °F; 447 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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[1] 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.[2]

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.[3]

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.[4]

Storage

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

Synthesis

The reaction of 1-methyl-4-piperidone [1445-73-4] (1) with hydrogen sulphide gas gives 1-methylpiperidine-4,4-dithiol [87225-55-6] (2). The reduction of this reactive intermediate over sodium borohydride leads to 1-methylpiperidine-4-thiol [1072-99-7] (3). The reaction with ethyl chloroformate [541-41-3] gives at first PC13564015 (4). The addition of a second equivalent of reagent then leads to PC13564017 (5). Hydrolysis of both the thiocarbamate groups with hydroxonium ion led to Piperidine-4-thiol hydrochloride [99201-86-2] (6). Sodium hydride catalyzed alkylation of the thiol group with 2,6-Dichloropyridine [2402-78-0] (7) completed the synthesis of Anpirtoline (8).

References
  1. "Anpirtoline Hydrochloride". Chem-Info. Retrieved 2012-10-19.
  2. "Product Block - Chemicals - Serotonergics - Anpirtoline Hydrochloride". Santa Cruz Biotechnology, Inc. Retrieved 2012-10-19.
  3. "Product Block - Chemicals - Serotonergics - Anpirtoline Hydrochloride". Santa Cruz Biotechnology, Inc. Retrieved 2012-10-19.
  4. De Almeida, R. M.; Miczek, K. A. (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. EP0149088 idem Jurgen Engel, Vladimir Jakovlev, Bernd Nickel, Klaus Thiemer, Gerhard Scheffler, U.S. patent 4,643,995 (1987 to Degussa Aktiengesellschaft).
  6. Rádl, Stanislav; Hafner, Wieland; Hezký, Petr; Krejčí, Ivan; Proška, Jan; Taimr, Jan (1999). "Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic". Collection of Czechoslovak Chemical Communications. 64 (2): 363–376. doi:10.1135/cccc19990363.
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