Deserpidine

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Cat Number

API131011

CAS Number

131-01-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

131-01-1

EINECS

205-004-8

Storage

Under -20°C

Synonyms

methyl 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate;Harmonyl;Raunormine

Molecular Formula

C32H38N2O8

Molecular Weight

578.7

Smiles

CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC

Appearance

White to off-white solid

Melting Point

228-232℃

Boiling Point

638℃

Relative Density

1.2

General Description

Deserpidine is a naturally occurring indole alkaloid extracted from the roots of Rauwolfia serpentina. It is classified as a rauwolfia alkaloid with antihypertensive and tranquilizing properties, structurally related to reserpine but differing in its methoxy substitution pattern at the C-11 position.

Mechanism of Action

Deserpidine exerts its antihypertensive effect primarily through depletion of catecholamine stores (norepinephrine, dopamine, serotonin) in peripheral sympathetic nerve endings and the central nervous system. It also acts as a mild alpha-1 adrenergic receptor antagonist, contributing to vasodilatory effects.

Application

Indicated for the treatment of hypertension and anxiety. Deserpidine is a naturally occurring Rauwolfia alkaloid that depletes catecholamine stores in peripheral sympathetic nerve endings and the central nervous system, providing antihypertensive and tranquilizing effects.

An efficient six-step synthesis of Deserpidine from the more abundant and commercially available reserpine was developed, achieving a 41% overall yield. Deserpidine differs from reserpine only by the absence of a methoxy group at the C-11 position but has limited natural availability. Pharmacologically, deserpidine has been employed for the treatment of hypertension and as a tranquilizer. It also appears to act as a controller of other cardiac disorders. Like reserpine, deserpidine acts by depleting biogenic amines such as noradrenaline, dopamine, and serotonin. The key step in the synthesis is lactone ring formation, which allows regioselective cleavage of the C-11 methoxyl group without affecting the C-17 methoxy group.

Fig. 1 Synthesis of Deserpidine. (Varchi G.; et al. 2005)

References

Varchi G, et al. Synthesis of deserpidine from reserpine. Journal of natural products, 2005, 68(11): 1629-1631.

What distinguishes Deserpidine from other Rauwolfia alkaloids such as reserpine?

Deserpidine has a methoxy substitution at C-11 instead of reserpine's trimethoxy pattern, resulting in distinct pharmacokinetic properties including a shorter duration of catecholamine depletion.

What storage conditions are required?

Must be stored under -20℃ in a tightly sealed container, protected from light and moisture.

What purity grade is available?

Supplied as a high-purity grade suitable for R&D and pharmaceutical manufacturing.

Can packaging and order options be customized?

Custom packaging options and flexible order quantities can be tailored to customer R&D and production requirements.