Calycanthine
(Synonyms: 腊梅碱) 目录号 : GC35596
Calycanthine 是从 Psychotria 属中分离出的花萼科生物碱，是一种中枢神经系统毒素，可引起抽搐。
Cas No.:595-05-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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].
[1]. AdjibadÉ Y, et al. Action of calycanthine on nervous transmission in cockroach central nervous system. Planta Med. 1991 Apr;57(2):99-101. [2]. Numan RW, et al. Wintersweet (Chimonanthus praecox) toxicity in four goats. N Z Vet J. 2016 May;64(3):179-81.
| Cas No. | 595-05-1 | SDF | |
| 别名 | 腊梅碱 | ||
| Canonical SMILES | CN1CC[C@]23C4=CC=CC=C4N[C@@]1([H])[C@@]25C6=CC=CC=C6N[C@]3([H])N(C)CC5 | ||
| 分子式 | C22H26N4 | 分子量 | 346.47 |
| 溶解度 | DMSO : 100 mg/mL (288.63 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.8863 mL | 14.4313 mL | 28.8625 mL |
| 5 mM | 0.5773 mL | 2.8863 mL | 5.7725 mL |
| 10 mM | 0.2886 mL | 1.4431 mL | 2.8863 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Convulsant actions of Calycanthine
Toxicol Appl Pharmacol 2003 Jul 1;190(1):58-64.PMID:12831783DOI:10.1016/s0041-008x(03)00149-2.
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.
Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine
J Org Chem 2015 Oct 16;80(20):10309-16.PMID:26402317DOI:10.1021/acs.joc.5b01907.
Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (-)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the Calycanthine skeleton was observed and facilitated the synthesis of (-)-calycanthine (3).
Action of Calycanthine on nervous transmission in cockroach central nervous system
Planta Med 1991 Apr;57(2):99-101.PMID:1653964DOI:10.1055/s-2006-960040.
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.
[Alkaloids of Pausinystalia macroceras]
Planta Med 1981 Apr;41(4):374-8.PMID:17401858DOI:10.1055/s-2007-971729.
A study of the alkaloidal content of trunk-barks of Pausinystalia macroceras (K. Schum.) Pierre, Rubiaceae, resulted in the isolation of six alkaloids, five of which are indole alkaloids that belong to the yohimbane and heteroyohimbane groups; among them, yohimbine was found in major amount. Moreover, the levorotatory isomer of Calycanthine, a quinoline dimeric tryptophane derived base, has been isolated for the first time. The phytochemical significance of Calycanthine and related alkaloids is discussed.
Wintersweet (Chimonanthus praecox) toxicity in four goats
N Z Vet J 2016 May;64(3):179-81.PMID:26503546DOI:10.1080/00480169.2015.1111779.
Case history: A one-year-old female goat presented with acute onset of recumbency, seizures and vocalisation approximately 5 hours after being given access to branch trimmings from a neighbour's garden. The plant from which the pruned branches came was subsequently identified as wintersweet (Chimonanthus praecox). Three other goats kept in the same paddock displayed similar clinical signs over a period of 4 hours following the initial presentation. Clinical findings: All four goats were ataxic, displayed tetanic seizures and were in lateral recumbency; they had dilated pupils and were hyperaesthetic, with elevated heart and respiratory rates. After symptomatic treatment, including sedation with diazepam, one of the three goats continued to deteriorate and was subjected to euthanasia. The remaining three goats recovered over 1-14 days with nursing care and physiotherapy. Diagnosis: Toxicity due to ingestion of wintersweet, which contains the alkaloid Calycanthine. Clinical relevance: Calycanthine is a central nervous system toxin, causing convulsions. Wintersweet shrubs are present in many New Zealand gardens. Practitioners should be aware that the seeds and flowers, and possibly the leaves, of this plant are highly toxic with signs of toxicity including ataxia, hyperaesthesia and seizures.