Chiral Switches of Tramadol Hydrochloride, a Potential Psychedelic Drug─Past and Future

Israel Agranat; Ilaria D’Acquarica

doi:10.1021/acsmedchemlett.4c00322

Chiral Switches of Tramadol Hydrochloride, a Potential Psychedelic Drug─Past and Future

Israel Agranat^*, Ilaria D’Acquarica^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Review article › peer-review

1 Scopus citations

Abstract

The chiral opioid analgesic tramadol was patented (1962) as a cis- and trans-racemates mixture. A first chiral switch led to the (±)-cis-(1RS,2RS) racemate, patented and approved as Tramal (1980), preferred over the (+)-cis-(1R,2R)-enantiomer. Consecutive chiral switches of (±)-cis-tramadol to (+)-cis-(1R,2R)-tramadol/salts were patented. This Viewpoint calls for developing (+)-cis-(1R,2R)-tramadol medicines and recognizing tramadol medicines as potential psychedelics to overcome the spreading tramadol crisis.

Original language	English
Pages (from-to)	1409-1416
Number of pages	8
Journal	ACS Medicinal Chemistry Letters
Volume	15
Issue number	9
DOIs	https://doi.org/10.1021/acsmedchemlett.4c00322
State	Published - 12 Sep 2024

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

Keywords

Analgesics
Chiral Switch
Opioid Crisis
Patents
Psychedelic
Stereochemistry
Tramadol

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10.1021/acsmedchemlett.4c00322

Cite this

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title = "Chiral Switches of Tramadol Hydrochloride, a Potential Psychedelic Drug─Past and Future",

abstract = "The chiral opioid analgesic tramadol was patented (1962) as a cis- and trans-racemates mixture. A first chiral switch led to the (±)-cis-(1RS,2RS) racemate, patented and approved as Tramal (1980), preferred over the (+)-cis-(1R,2R)-enantiomer. Consecutive chiral switches of (±)-cis-tramadol to (+)-cis-(1R,2R)-tramadol/salts were patented. This Viewpoint calls for developing (+)-cis-(1R,2R)-tramadol medicines and recognizing tramadol medicines as potential psychedelics to overcome the spreading tramadol crisis.",

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doi = "10.1021/acsmedchemlett.4c00322",

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N2 - The chiral opioid analgesic tramadol was patented (1962) as a cis- and trans-racemates mixture. A first chiral switch led to the (±)-cis-(1RS,2RS) racemate, patented and approved as Tramal (1980), preferred over the (+)-cis-(1R,2R)-enantiomer. Consecutive chiral switches of (±)-cis-tramadol to (+)-cis-(1R,2R)-tramadol/salts were patented. This Viewpoint calls for developing (+)-cis-(1R,2R)-tramadol medicines and recognizing tramadol medicines as potential psychedelics to overcome the spreading tramadol crisis.

AB - The chiral opioid analgesic tramadol was patented (1962) as a cis- and trans-racemates mixture. A first chiral switch led to the (±)-cis-(1RS,2RS) racemate, patented and approved as Tramal (1980), preferred over the (+)-cis-(1R,2R)-enantiomer. Consecutive chiral switches of (±)-cis-tramadol to (+)-cis-(1R,2R)-tramadol/salts were patented. This Viewpoint calls for developing (+)-cis-(1R,2R)-tramadol medicines and recognizing tramadol medicines as potential psychedelics to overcome the spreading tramadol crisis.

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KW - Stereochemistry

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Chiral Switches of Tramadol Hydrochloride, a Potential Psychedelic Drug─Past and Future

Abstract

Bibliographical note

Keywords

UN SDGs

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