Shipping to United States We Offer Worldwide Shipping
Login Wishlist

Calycanthine

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0228

  • Specification : 99.0%(HPLC)

  • CAS number : 595-05-1

  • Formula : C22H26N4

  • Molecular Weight : 346.47

  • PUBCHEM ID : 5392245

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-P0228

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC)

Storage

2-8°C

Molecular Weight

346.47

Appearance

Powder

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CCC23C4NC5=CC=CC=C5C2(C1NC6=CC=CC=C36)CCN4C

Synonyms

(1S,3R)-N-Boc-3-aminocyclopentanecarboxylic acid/(1S,3R)-cyclopentanecarboxylic acid 3-[[(1,1-dimethylethoxy)carbonyl]amino]/(1S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid/(+)-(1S,3R)-N-Boc-b-homocycloleucine/Calycanthin/(1R,3S)-N-boc-1-Aminocyclopentane-3-carboxylicacid(e.e.)/(1S,3R)-3-amino-N-tert-butyloxycarbonylcyclopentanecarboxylic acid/(-)-(1R,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID/(1S,3R)-(+)-3-(BOC-AMINO)CYCLOPENTANECARBOXYLIC ACID/CALYCANTHINE/(+)-(1S,3R)-N-Boc-3-aMinocyclopentanecarboxylic acidacid

IUPAC Name

(1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetrazahexacyclo[9.7.3.32,10.01,10.04,9.013,18]tetracosa-4,6,8,13,15,17-hexaene

Applications

Calycanthine, the principal alkaloid of the order Calycanthaceae, has been isolated from a species of the genus Psychotria, and is a central nervous system toxin, causing convulsions[1][2].

Density

1.29g/cm3

Solubility

Methanol; Chloroform; Ethyl Acetate

Flash Point

310.3ºC

Boiling Point

531.8ºC at 760mmHg

Melting Point

245° (evac tube)

InChl

InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

InChl Key

XSYCDVWYEVUDKQ-GXRSIYKFSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:595-05-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

12831783

Abstract

The principal alkaloid of the family Calycanthaceae, calycanthine has long been recognized as a central convulsant. The alkaloid inhibited the potassium-stimulated release of [(3)H]GABA from slices of rat hippocampus with an ED(50) of approximately 21 microM. This effect appeared to be moderately selective since calycanthine at 100 microM had only a weak effect on the potassium-stimulated release of [(3)H]acetylcholine (15%) and no significant effects on the release of [(3)H]D-aspartate from hippocampal and cerebellar slices or the release of [(3)H]glycine from spinal cord slices. Calycanthine blocked the L-type calcium currents with an IC(50) of approximately 42 microM and also weakly inhibited the N-type calcium currents (IC(50) > 100 microM) from neuroblastoma X glioma cells, suggesting voltage-dependent calcium channel blockade as a possible mechanism for its inhibition of GABA and ACh release. Calycanthine was also found to directly inhibit GABA-mediated currents (K(B) approximately 135 microM) from human alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes but had no effect at 100 microM on human rho(1) GABA(c) receptors. The results indicated that calycanthine may mediate its convulsant action predominantly by inhibiting the release of the inhibitory neurotransmitter GABA as a result of interactions with L-type Ca(2+) channels and by inhibiting GABA-mediated chloride currents at GABA(A) receptors.

Title

Convulsant actions of calycanthine.

Author

Chebib M1, Duke RK, Duke CC, Connor M, Mewett KN, Johnston GA.

Publish date

2003 Jul 1

PMID

22499409

Title

Catalytic asymmetric total synthesis of chimonanthine, folicanthine, and calycanthine through double Michael reaction of bisoxindole.

Author

Mitsunuma H1, Shibasaki M, Kanai M, Matsunaga S.

Publish date

2012 May 21

PMID

1653964

Abstract

Calycanthine, the principal alkaloid of the order Calycanthaceae, has been isolated from a species of the genus Psychotria (Rubiaceae) occurring in some Pacific islands. The drug is considered as a very powerful convulsant poison but very little is known about its mechanism of action. The symptoms observed were similar to those of some neuropoisons such as strychnine. The properties of this alkaloid have been investigated on the genesis, conduction, and transmission of the nerve impulse, using giant axons of the cockroach (Periplaneta americana). Calycanthine hydrochloride (10(-5) M), which did not alter nervous conduction in pre- and post-synaptic fibers, significantly reduced the efficacy of the synaptic transmission.

Title

Action of calycanthine on nervous transmission in cockroach central nervous system.

Author

Adjibade Y1, Hue B, Pelhate M, Anton R.

Publish date

1991 Apr