Geissoschizine methyl ether

Name: Geissoschizine methyl ether
Brand: MedChemExpress
SKU: HY-N2411
Rating: 4.5 (1 reviews)

Cat. No.: HY-N2411 Purity: 99.97%: Data Sheet
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Geissoschizine methyl ether is an orally active, blood-brain barrier permeable alkaloid, and a partial agonist of the 5-HT₁A receptor. It can be isolated from Uncaria hook. Geissoschizine methyl ether potently inhibits the binding of [³H]8-OH-DPAT to the 5-HT₁A receptor in a concentration-dependent manner, with an IC₅₀ of 0.904 μM. It ameliorates isolation-induced increased aggression and reduced sociability in mice. Geissoschizine methyl ether promotes oligodendrocyte differentiation and remyelination in the medial prefrontal cortex of adult mice.

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Geissoschizine methyl ether Chemical Structure

CAS No. : 60314-89-8

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5 mg	In-stock	Estimated Time of Arrival: December 31
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Based on 1 publication(s) in Google Scholar

1 Publications Citing Use of MCE Geissoschizine methyl ether

•Plant Biotechnol (Tokyo). 2025 Jun 25;42(2):145-154. [Abstract]

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5-HT Receptor 5-HT₁ Receptor 5-HT₂ Receptor 5-HT₃ Receptor 5-HT₄ Receptor 5-HT₅ Receptor 5-HT₆ Receptor 5-HT₇ Receptor

Biological Activity
Purity & Documentation
References
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Description

IC₅₀ & Target^[1]

5-HT_1A Receptor

0.904 μM (IC₅₀)

In Vitro

Geissoschizine methyl ether (0.01-100 μM) potently inhibits the binding of [³H]8-OH-DPAT to 5-HT₁A receptors in a concentration-dependent manner, with an IC₅₀ of 0.904 μM and a K_i of 0.517 μM^[2].
Geissoschizine methyl ether (0.1-100 μM; 20 min preincubation) acts as a partial agonist of the 5-HT_1A receptor in CHO-h5-HT_1A cell membranes, and induces approximately 40% of the maximal [³⁵S]GTPγS binding activity triggered by the full agonist 5-HT^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Geissoschizine methyl ether (150-300 µg/kg; p.o.; once daily; for 14 consecutive days) significantly ameliorates isolation-induced enhanced aggression and reduced sociability in male ddY mice, and its effects are mediated by the 5-HT_1A receptor^[2].
Geissoschizine methyl ether (0.3 mg/kg; p.o.; once daily; for 14 consecutive days) increases the generation of mature oligodendrocytes in the medial prefrontal cortex of cuprizone-induced demyelinated adult male C57BL/6J mice, and restores MBP immunoreactivity to approximately 85% of the control level^[3].
Geissoschizine methyl ether (0.3 mg/kg; p.o.; once daily; for 14 consecutive days) exerts no effect on myelination or proliferating cell populations in the medial prefrontal cortex of healthy adult male C57BL/6J mice^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	ddY (male, 4 weeks old at acquisition, habituated 1 week, isolation-housed 4 weeks to induce behavioral changes)^[2]
Dosage:	75 µg/kg (single dose); 150 µg/kg (single dose; 14-day repeated dose); 300 µg/kg (single dose; 14-day repeated dose; 15-day coadministration)
Administration:	p.o.; single dose; once daily for 14 days; once daily for 15 days
Result:	Significantly ameliorated isolation-induced decreased social behavior at 300 µg/kg single dose (P<0.01), with no effect on aggressive behavior at any single dose tested. Significantly decreased isolation-induced increased aggressive behavior (P<0.01) and increased isolation-induced decreased social behavior (P<0.01) at 150 µg/kg and 300 µg/kg with 14-day repeated administration. Counteracted the ameliorative effects of 14-day repeated GM administration on aggressive and social behaviors when 0.1 mg/kg WAY-100635 was given i.p. 30 minutes after final GM dose (P<0.01). Counteracted the ameliorative effects of 300 µg/kg GM on aggressive and social behaviors when coadministered with 0.1 mg/kg WAY-100635 for 14 days (P<0.05). Sustained ameliorative effects on aggressive (P<0.05) and social (P<0.01) behaviors on day 15 without GM administration at 300 µg/kg 14-day repeated dose. Caused no significant changes in motor activity in any treated groups compared to controls.

Animal Model:	C57BL/6J (adult male, aged 57-113 days, demyelination induced by 0.2% cuprizone-containing chow for 4 weeks)^[3]
Dosage:	0.3 mg/kg
Administration:	p.o.; once daily; 14 days
Result:	Increased the number of BrdU-labeled GSTpi⁺ mature oligodendrocytes to 21.1/mm². Restored MBP immunoreactivity to 85.19% of control levels. Restored the ratio of MBP to neurofilament (NF) intensity to 0.28. Showed no significant effect on body weight, the number of BrdU-labeled NG2⁺ oligodendrocyte progenitor cells, BrdU-labeled Iba1⁺ microglial cells, or total GSTpi⁺ mature oligodendrocytes.

Molecular Weight

366.45

Formula

C₂₂H₂₆N₂O₃

CAS No.

60314-89-8

Appearance

Solid

Color

White to off-white

SMILES

COC(/C([C@H]1C[C@@]2([H])C3=C(CCN2C/C1=C/C)C4=CC=CC=C4N3)=C\OC)=O

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL (272.89 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.7289 mL	13.6444 mL	27.2889 mL
5 mM	0.5458 mL	2.7289 mL	5.4578 mL
10 mM	0.2729 mL	1.3644 mL	2.7289 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Purity: 99.97%

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Data Sheet (284 KB) SDS (393 KB)

COA (256 KB) RP-HPLC (262 KB) MS (69 KB)

Handling Instructions (2659 KB)

References

[1]. Matsumoto T, et al. In vitro identification of human cytochrome P450 isoforms involved in the metabolism of Geissoschizine methyl ether, an active component of the traditional Japanese medicine Yokukansan. Xenobiotica. 2016;46(4):325-34. [Content Brief]

[2]. Nishi A, et al. Geissoschizine methyl ether, an alkaloid in Uncaria hook, is a potent serotonin ₁A receptor agonist and candidate for amelioration of aggressiveness and sociality by yokukansan. Neuroscience. 2012 Apr 5;207:124-36. [Content Brief]

[3]. Morita S, et al. Geissoschizine methyl ether, an alkaloid from the Uncaria hook, improves remyelination after cuprizone-induced demyelination in medial prefrontal cortex of adult mice. Neurochem Res. 2014;39(1):59-67.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	2.7289 mL	13.6444 mL	27.2889 mL	68.2221 mL
	5 mM	0.5458 mL	2.7289 mL	5.4578 mL	13.6444 mL
	10 mM	0.2729 mL	1.3644 mL	2.7289 mL	6.8222 mL
	15 mM	0.1819 mL	0.9096 mL	1.8193 mL	4.5481 mL
	20 mM	0.1364 mL	0.6822 mL	1.3644 mL	3.4111 mL
	25 mM	0.1092 mL	0.5458 mL	1.0916 mL	2.7289 mL
	30 mM	0.0910 mL	0.4548 mL	0.9096 mL	2.2741 mL
	40 mM	0.0682 mL	0.3411 mL	0.6822 mL	1.7056 mL
	50 mM	0.0546 mL	0.2729 mL	0.5458 mL	1.3644 mL
	60 mM	0.0455 mL	0.2274 mL	0.4548 mL	1.1370 mL
	80 mM	0.0341 mL	0.1706 mL	0.3411 mL	0.8528 mL
	100 mM	0.0273 mL	0.1364 mL	0.2729 mL	0.6822 mL