4-Benzylpyridine
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MedKoo CAT#: 412115

CAS#: 2116-65-6

Description: 4-Benzylpyridine acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin.


Chemical Structure

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4-Benzylpyridine
CAS# 2116-65-6

Theoretical Analysis

MedKoo Cat#: 412115
Name: 4-Benzylpyridine
CAS#: 2116-65-6
Chemical Formula: C12H11N
Exact Mass: 169.0891
Molecular Weight: 169.227
Elemental Analysis: C, 85.17; H, 6.55; N, 8.28

Price and Availability

Size Price Availability Quantity
10.0g USD 220.0 2 Weeks
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Synonym: 4-Benzylpyridine; Ba33216; Ba-33216; Ba 33216

IUPAC/Chemical Name: 4-Benzylpyridine

InChi Key: DBOLXXRVIFGDTI-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H11N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-9H,10H2

SMILES Code: C1(CC2=CC=CC=C2)=CC=NC=C1

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: >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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 169.227 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

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1: Rajnák C, Titiš J, Moncol J, Mičová R, Boča R. Field-Induced Slow Magnetic Relaxation in a Mononuclear Manganese(II) Complex. Inorg Chem. 2019 Jan 22;58(2):991-994. doi: 10.1021/acs.inorgchem.8b02675. Epub 2019 Jan 9. PMID: 30624897.

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4: Shah MB, Pascual J, Zhang Q, Stout CD, Halpert JR. Structures of cytochrome P450 2B6 bound to 4-benzylpyridine and 4-(4-nitrobenzyl)pyridine: insight into inhibitor binding and rearrangement of active site side chains. Mol Pharmacol. 2011 Dec;80(6):1047-55. doi: 10.1124/mol.111.074427. Epub 2011 Aug 29. PMID: 21875942; PMCID: PMC3228530.

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6: Cong H, Tao LL, Yu YH, Tao Z, Yang F, Zhao YJ, Xue SF, Lawrance GA, Wei G. Interaction between tetramethylcucurbit[6]uril and some pyridine derivates. J Phys Chem A. 2007 Apr 12;111(14):2715-21. doi: 10.1021/jp066031j. Epub 2007 Mar 22. PMID: 17388386.

7: Korhonen LE, Turpeinen M, Rahnasto M, Wittekindt C, Poso A, Pelkonen O, Raunio H, Juvonen RO. New potent and selective cytochrome P450 2B6 (CYP2B6) inhibitors based on three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis. Br J Pharmacol. 2007 Apr;150(7):932-42. doi: 10.1038/sj.bjp.0707173. Epub 2007 Feb 26. PMID: 17325652; PMCID: PMC2013880.

8: Lotter M, Schilling J, Reimann E, Bracher F. First total synthesis of the 2,7-naphthyridine alkaloids lophocladine a and B. Arch Pharm (Weinheim). 2006 Dec;339(12):677-9. doi: 10.1002/ardp.200600134. PMID: 17109463.

9: Carson EC, Lippard SJ. Synthesis, characterization, and preliminary oxygenation studies of benzyl- and ethyl-substituted pyridine ligands of carboxylate-rich diiron(II) complexes. Inorg Chem. 2006 Jan 23;45(2):828-36. doi: 10.1021/ic051471v. PMID: 16411721; PMCID: PMC2505187.

10: Kobayashi Y, Matsuura Y, Kotani E, Fukuda T, Aoyagi T, Tobinaga S, Yoshida T, Kuroiwa Y. Structural requirements for the induction of hepatic microsomal cytochrome P450 by imidazole- and pyridine-containing compounds in rats. J Biochem. 1993 Nov;114(5):697-701. doi: 10.1093/oxfordjournals.jbchem.a124239. PMID: 8113223.

11: Kobayashi Y, Matsuura Y, Kotani E, Iio T, Fukuda T, Aoyagi T, Tobinaga S, Yoshida T, Kuroiwa Y. Induction of hepatic microsomal cytochrome P450 and drug- metabolizing enzymes by 4-benzylpyridine and its structurally related compounds in rats. Dose- and sex-related differential induction of cytochrome P450 species. Biochem Pharmacol. 1992 May 28;43(10):2151-9. doi: 10.1016/0006-2952(92)90174-h. PMID: 1599503.

12: Franklin MR. Drug metabolizing enzyme induction by simple diaryl pyridines; 2-substituted isomers selectively increase only conjugation enzyme activities, 4-substituted isomers also induce cytochrome P450. Toxicol Appl Pharmacol. 1991 Oct;111(1):24-32. doi: 10.1016/0041-008x(91)90130-7. PMID: 1949033.

13: Matsuura Y, Kotani E, Iio T, Fukuda T, Tobinaga S, Yoshida T, Kuroiwa Y. Structure-activity relationships in the induction of hepatic microsomal cytochrome P450 by clotrimazole and its structurally related compounds in rats. Biochem Pharmacol. 1991 Jun 15;41(12):1949-56. doi: 10.1016/0006-2952(91)90135-r. PMID: 2039545.

14: Arai Y, Hamamichi N, Kinemuchi H. Time-dependent inhibition of rat brain monoamine oxidase by an analogue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine. Neurosci Lett. 1986 Oct 8;70(2):255-60. doi: 10.1016/0304-3940(86)90473-8. PMID: 3490636.

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Additional Information

4-Benzylpyridine is most efficacious as a releaser of norepinephrine, with an ec50 of 109/41.4/5246nM for DA/NE/5HT, respectively .[1] It has a fast onset of action and a short duration.[1] It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.[2]