WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329862
CAS#: 498-96-4 (free base)
Description: Guvacine is a GABA uptake inhibitor. Guvacine competitively inhibits GABA uptake (IC50 = 10 μM; Ki = 14 μM) in rat hippocampal brain slices.
Hodoodo Cat#: H329862
Name: Guvacine free base
CAS#: 498-96-4 (free base)
Chemical Formula: C7H11NO2
Exact Mass: 141.08
Molecular Weight: 141.170
Elemental Analysis: C, 59.56; H, 7.85; N, 9.92; O, 22.67
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.
Related CAS #: 498-96-4 (free base) 6197-39-3 (Norarecoline HCl) 6027-91-4 (HCl),
Synonym: Guvacine free base; Guvacoline;
IUPAC/Chemical Name: 1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride
InChi Key: DYPLDWLIOGXSSE-UHFFFAOYSA-N
InChi Code: InChI=1S/C7H11NO2/c1-10-7(9)6-3-2-4-8-5-6/h3,8H,2,4-5H2,1H3
SMILES Code: O=C(C1=CCCNC1)OC
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 141.17 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Pavia MR, Lobbestael SJ, Nugiel D, Mayhugh DR, Gregor VE, Taylor CP, Schwarz RD, Brahce L, Vartanian MG. Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake. J Med Chem. 1992 Oct 30;35(22):4238-48. PubMed PMID: 1433224.
2: Wolf-Pflugmann M, Lambrecht G, Wess J, Mutschler E. Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester. Arzneimittelforschung. 1989 May;39(5):539-44. PubMed PMID: 2757669.
3: Falch E, Meldrum BS, Krogsgaard-Larsen P. GABA uptake inhibitors. Synthesis and effects on audiogenic seizures of ester prodrugs of nipecotic acid, guvacine and cis-4-hydroxynipecotic acid. Drug Des Deliv. 1987 Sep;2(1):9-21. PubMed PMID: 3509345.
4: Lodge D, Johnston GA, Curtis DR, Brand SJ. Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain Res. 1977 Nov 18;136(3):513-22. PubMed PMID: 922499.
5: Knutsen LJ, Andersen KE, Lau J, Lundt BF, Henry RF, Morton HE, Naerum L, Petersen H, Stephensen H, Suzdak PD, Swedberg MD, Thomsen C, Sørensen PO. Synthesis of novel GABA uptake inhibitors. 3. Diaryloxime and diarylvinyl ether derivatives of nipecotic acid and guvacine as anticonvulsant agents. J Med Chem. 1999 Sep 9;42(18):3447-62. PubMed PMID: 10479278.
6: McELVAIN SM, STORK G. Piperidine derivatives; the preparation of l-benzoyl-3-carbethoxy-4-piperidone; a synthesis of guvacine. J Am Chem Soc. 1946 Jun;68:1049-53. PubMed PMID: 20985618.
7: Voigt V, Laug L, Zebisch K, Thondorf I, Markwardt F, Brandsch M. Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1). J Pharm Pharmacol. 2013 Apr;65(4):582-90. doi: 10.1111/jphp.12006. Epub 2012 Nov 19. PubMed PMID: 23488788.
8: Yu H, Tang L, Wu H, Wang K, Cai B, Zhang X, Zhang C, Yin Y. Determination of contents of four alkaloids in Pericarpium arecae by quantitative analysis of multi-components by single-marker. Pak J Pharm Sci. 2016 Jul;29(4):1269-74. PubMed PMID: 27393441.
9: Larsson OM, Falch E, Krogsgaard-Larsen P, Schousboe A. Kinetic characterization of inhibition of gamma-aminobutyric acid uptake into cultured neurons and astrocytes by 4,4-diphenyl-3-butenyl derivatives of nipecotic acid and guvacine. J Neurochem. 1988 Mar;50(3):818-23. PubMed PMID: 3339356.
10: Srimany A, George C, Naik HR, Pinto DG, Chandrakumar N, Pradeep T. Developmental patterning and segregation of alkaloids in areca nut (seed of Areca catechu) revealed by magnetic resonance and mass spectrometry imaging. Phytochemistry. 2016 May;125:35-42. doi: 10.1016/j.phytochem.2016.02.002. Epub 2016 Feb 17. PubMed PMID: 26896852.
11: Mantegazza P, Tammiso R, Vicentini L, Zambotti F, Zonta N. Nipecotic acid and guvacine antagonism on morphine analgesia in rats. Pharmacol Res Commun. 1979 Sep;11(8):657-62. PubMed PMID: 515113.
12: Yu HL, Tang LJ, Wu H, Mao CQ, Lu TL, Mao SH. [Optimization of Preparation of Cutting-processed Arecae Pericarpium with Multi-index Orthogonal Method]. Zhong Yao Cai. 2014 Dec;37(12):2178-81. Chinese. PubMed PMID: 26080498.
13: Jaw SP, Nguyen B, Vuong QT, Trinh TA, Nguyen M, Truong DD. Effects of GABA uptake inhibitors on posthypoxic myoclonus in rats. Brain Res Bull. 1996;39(3):189-92. PubMed PMID: 8866696.
14: Rasmussen RN, Lagunas C, Plum J, Holm R, Nielsen CU. Interaction of GABA-mimetics with the taurine transporter (TauT, Slc6a6) in hyperosmotic treated Caco-2, LLC-PK1 and rat renal SKPT cells. Eur J Pharm Sci. 2016 Jan 20;82:138-46. doi: 10.1016/j.ejps.2015.11.020. Epub 2015 Nov 26. PubMed PMID: 26631583.
15: Yuan J, Yang D, Liang Y, Gao W, Ren Z, Zeng W, Wang B, Han J, Guo D. Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro. J Food Sci. 2012 Apr;77(4):T70-8. doi: 10.1111/j.1750-3841.2012.02653.x. PubMed PMID: 22515256.
16: Franke AA, Li X, Lai JF. Pilot study of the pharmacokinetics of betel nut and betel quid biomarkers in saliva, urine, and hair of betel consumers. Drug Test Anal. 2016 Oct;8(10):1095-1099. doi: 10.1002/dta.1912. Epub 2015 Dec 1. PubMed PMID: 26619803; PubMed Central PMCID: PMC4967029.
17: Franke AA, Mendez AJ, Lai JF, Arat-Cabading C, Li X, Custer LJ. Composition of betel specific chemicals in saliva during betel chewing for the identification of biomarkers. Food Chem Toxicol. 2015 Jun;80:241-6. doi: 10.1016/j.fct.2015.03.012. Epub 2015 Mar 19. PubMed PMID: 25797484; PubMed Central PMCID: PMC4454402.
18: Chattopadhyay A, Ray JG. Molecular Pathology of Malignant Transformation of Oral Submucous Fibrosis. J Environ Pathol Toxicol Oncol. 2016;35(3):193-205. Review. PubMed PMID: 27910776.
19: Virmani MA, Conti R, Spadoni A, Rossi S, Arrigoni-Martelli E. Inhibition of L-carnitine uptake into primary rat cortical cell cultures by GABA and GABA uptake blockers. Pharmacol Res. 1995 Mar-Apr;31(3-4):211-5. PubMed PMID: 7630861.
20: Kern FT, Wanner KT. Generation and screening of oxime libraries addressing the neuronal GABA transporter GAT1. ChemMedChem. 2015 Feb;10(2):396-410. doi: 10.1002/cmdc.201402376. Epub 2014 Nov 4. PubMed PMID: 25369775.
