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MedKoo Cat#: 413222 | Name: Coclaurine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids.

Chemical Structure

Coclaurine
Coclaurine
CAS#486-39-5

Theoretical Analysis

MedKoo Cat#: 413222

Name: Coclaurine

CAS#: 486-39-5

Chemical Formula: C17H19NO3

Exact Mass: 285.1365

Molecular Weight: 285.34

Elemental Analysis: C, 71.56; H, 6.71; N, 4.91; O, 16.82

Price and Availability

Size Price Availability Quantity
5mg USD 700.00 2 Weeks
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Related CAS #
No Data
Synonym
Coclaurine; Machiline; (S)-Coclaurine, (–)-Coclaurine
IUPAC/Chemical Name
(1S)-1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol
InChi Key
LVVKXRQZSRUVPY-HNNXBMFYSA-N
InChi Code
InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
SMILES Code
OC1=CC2=C(C=C1OC)CCN[C@H]2CC3=CC=C(O)C=C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 285.34 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
1: Bennett MR, Thompson ML, Shepherd SA, Dunstan MS, Herbert AJ, Smith DRM, Cronin VA, Menon BRK, Levy C, Micklefield J. Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase. Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10600-10604. doi: 10.1002/anie.201805060. Epub 2018 Jun 28. PMID: 29791083; PMCID: PMC6099451. 2: Ali R, Jiao Y, Kerr Wall P, Patching SG, Ahmad I, Lutfulla G, dePamphilis CW. In silico identification and structure function analysis of a putative coclaurine N-methyltransferase from Aristolochia fimbriata. Comput Biol Chem. 2020 Apr;85:107201. doi: 10.1016/j.compbiolchem.2020.107201. Epub 2020 Jan 11. PMID: 31986303. 3: Okano M, Sato M, Kageyama S. Determination of higenamine and coclaurine levels in human urine after the administration of a throat lozenge containing Nandina domestica fruit. Drug Test Anal. 2017 Nov;9(11-12):1788-1793. doi: 10.1002/dta.2258. Epub 2017 Sep 15. PMID: 28801989. 4: Morishige T, Choi KB, Sato F. In vivo bioconversion of tetrahydroisoquinoline by recombinant coclaurine N-methyltransferase. Biosci Biotechnol Biochem. 2004 Apr;68(4):939-41. doi: 10.1271/bbb.68.939. PMID: 15118328. 5: Choi KB, Morishige T, Sato F. Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells. Phytochemistry. 2001 Apr;56(7):649-55. doi: 10.1016/s0031-9422(00)00481-7. PMID: 11314949. 6: Choi KB, Morishige T, Shitan N, Yazaki K, Sato F. Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica. J Biol Chem. 2002 Jan 4;277(1):830-5. doi: 10.1074/jbc.M106405200. Epub 2001 Oct 26. PMID: 11682473. 7: Watanabe H, Ikeda M, Watanabe K, Kikuchi T. Effects on central dopaminergic systems of d-coclaurine and d-reticuline, extracted from Magnolia salicifolia. Planta Med. 1981 Jul;42(3):213-22. doi: 10.1055/s-2007-971630. PMID: 7280087. 8: Watanabe H, Watanabe K, Kikuchi T. Effects of d-coclaurine and d-reticuline, benzyltetrahydroisoquinoline alkaloids, on levels of 3,4-dihydroxyphenylacetic acid and homovanillic acid in the mouse striatum. J Pharmacobiodyn. 1983 Oct;6(10):793-6. doi: 10.1248/bpb1978.6.793. PMID: 6141236. 9: Sowemimo BO, Beal JL, Doskotch RW, Svoboda GH. The isolation of stepharine and coclaurine from Sarcopetalum harveyanum. Lloydia. 1972 Mar;35(1):90-1. PMID: 5037484. 10: Kimura M, Kimura I, Takahashi K. The neuromuscular blocking actions of coclaurine derivatives and of paeoniflorin derivatives. Planta Med. 1982 Jul;45(3):136. doi: 10.1055/s-2007-971276. PMID: 17396817. 11: Feng YP, Jia HJ, Zhang LY, Zeng GY. [Effects of dl-demethyl coclaurine on beta-adrenergic receptors and adenylate cyclase in turkey erythrocyte membrane]. Yao Xue Xue Bao. 1982 Sep;17(9):641-6. Chinese. PMID: 6130668. 12: Bian Z, Zhang W, Tang J, Fei Q, Hu M, Chen X, Su L, Fei C, Ji D, Mao C, Tong H, Yuan X, Lu T. Mechanisms Underlying the Action of Ziziphi Spinosae Semen in the Treatment of Insomnia: A Study Involving Network Pharmacology and Experimental Validation. Front Pharmacol. 2021 Dec 24;12:752211. doi: 10.3389/fphar.2021.752211. PMID: 35002696; PMCID: PMC8740267. 13: Thavamani BS, Mathew M, Dhanabal SP. Cocculus hirsutus: Molecular Docking to Identify Suitable Targets for Hepatocellular Carcinoma by In silico Technique. Pharmacogn Mag. 2016 May;12(Suppl 3):S350-2. doi: 10.4103/0973-1296.185769. PMID: 27563224; PMCID: PMC4971956. 14: LU ST. [Studies on the alkaloids of Formosan louraceous plants. II. Alkaloids of Machilus kusanoi Hayata. (2). The isolation of di-coclaurine]. Yakugaku Zasshi. 1963 Jan;83:19-21. Japanese. doi: 10.1248/yakushi1947.83.1_19. PMID: 13931345. 15: Kimura I, Chui LH, Fujitani K, Kikuchi T, Kimura M. Inotropic effects of (+/-)-higenamine and its chemically related components, (+)-R-coclaurine and (+)-S-reticuline, contained in the traditional sino-Japanese medicines "bushi" and "shin-i" in isolated guinea pig papillary muscle. Jpn J Pharmacol. 1989 May;50(1):75-8. doi: 10.1254/jjp.50.75. PMID: 2724702. 16: Majrashi TA, Zulfiqar F, Chittiboyina AG, Ali Z, Khan IA. Isoquinoline alkaloids from Asimina triloba. Nat Prod Res. 2019 Oct;33(19):2823-2829. doi: 10.1080/14786419.2018.1504045. Epub 2018 Nov 20. PMID: 30453785. 17: Fridrichsons J, Mathieson AM. The crystal structure of coclaurine hydrobromide monohydrate and the absolute configuration of coclaurine. Tetrahedron. 1968 Sep;24(17):5785-9. doi: 10.1016/s0040-4020(01)96309-4. PMID: 5713420. 18: Kametani T, Takano S, Masuko K, Kuribara S. [Coclaurine and related compounds. I. Syntheses of dl-coclaurine and dl-O-benzyl-N-methylcoclaurine. (Studies on the syntheses of heterocyclic compounds 103.)]. Yakugaku Zasshi. 1965 Feb;85(2):166-8. Japanese. PMID: 5895296. 19: Chandrashekar K, Rajagopal P, Jh SF, Radhakrishnan S, Krishnan Muthaiah VP, Sontakke BR, Deshmukh VR, Periyasamy V, Muthiyan GG, Tarnekar AM, Gugapriya TS, Laxman PA, Tripathi SC, Jayaraman S. Molecular docking analysis of glycogen phosphorylase with inhibitors from Cissampelos pareira Linn. Bioinformation. 2021 Oct 31;17(10):866-869. doi: 10.6026/97320630017866. PMID: 35574507; PMCID: PMC9070628. 20: Baldas J, Bick IR, Falco MR, De Vries JX, Porter QN. Mass spectrometry of bisbenzylisoquinoline alkaloids. II. Alkaloids derived from one coclaurine and one isococlaurine unit. J Chem Soc Perkin 1. 1972;4:597-9. doi: 10.1039/p19720000597. PMID: 5066084.