4-HTMPIPO

Formula

C₂₁H₃₁NO₂

Molar mass

329.24 g·mol⁻¹

CAS

1445751-38-1

PubChem CID

72720476

Origin

A wholly synthetic compound with no natural occurrence. It appears as a transformation product of UR-144 in preparations intended for the illicit market, rather than as a substance deliberately manufactured for itself.

InChIKey

GWHGUYKAGQLPTQ-UHFFFAOYSA-N

Editorial estimate, not clinical.

4-HTMPIPO illustrates a barely visible phenomenon of the synthetic cannabinoid market: what a product contains is not always what its maker put into it. Kavanagh and colleagues analysed in 2013 products sold on the internet, in plant, resin and powder form, containing UR-144. They found six related compounds there, the most abundant being this one: the product of the addition of a molecule of water to the cyclopropane ring of UR-144, a transformation that opens that strained ring and converts it into a chain bearing a tertiary alcohol. The authors show that this compound is not itself stable: it cyclises into a dihydrofuran derivative, which re-forms depending on the acidity of the medium, and it also appears as an artefact during analysis by gas chromatography. Pyrolysis, that is what actually happens when the product is smoked, generates yet other molecules, common to this compound and to UR-144. The picture that emerges is that of an unstable mixture: what the user inhales is neither what was sold nor what was analysed. The pharmacological question remains entirely open, and that is the honest limit of this entry: no measurement of activity at cannabinoid receptors has been published for this compound. One can reason that opening the compact cyclopropane of UR-144 into a flexible, polar chain ought to reduce affinity, since that motif is precisely the one that anchors in the receptor pocket, but nothing has verified it.

An entirely chemical origin, described here by class only. The molecule derives from UR-144 by opening of its cyclopropane ring under the effect of an addition of water, a reaction that turns the tetramethylcyclopropyl group into a pentanone chain bearing a tertiary alcohol. The rest of the structure is unchanged: a ketone at position 3 of an indole whose nitrogen bears a pentyl chain. Kavanagh and colleagues moreover describe its reversible cyclisation into dihydrofuran derivatives, and its transformation by pyrolysis.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

Synthetic cannabinoid (SCRA)

Origin

A wholly synthetic compound with no natural occurrence. It appears as a transformation product of UR-144 in preparations intended for the illicit market, rather than as a substance deliberately manufactured for itself.

Status

Unscheduled

1. 1.Kavanagh et coll. 2013 : l'UR-144 dans les produits vendus par internet, identification des composés apparentés et caractérisation des produits de pyrolysePMID 23315949