Glaucine

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Glaucine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
  • (S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
JSmol)
  • CN1CCc2cc(c(c-3c2[C@@H]1Cc4c3cc(c(c4)OC)OC)OC)OC
  • InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1 ☒N
  • Key:RUZIUYOSRDWYQF-HNNXBMFYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Glaucine (1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum,[1] Glaucium oxylobum and Corydalis yanhusuo,[2][3] and in other plants like Croton lechleri in the family Euphorbiaceae.[4]

It has

positive allosteric modulator of the 5-HT2A receptor, which is also associated with the hallucinogenic effects of substances such as psilocybin and mescaline
.

Chemistry

Stereoisomerism

It was believed that only the (S)-form of glaucine occurs in nature until (R)-glaucine was found in fire poppy (Papaver californicum).[13]

Glaucine
(2 stereoisomers)
(S)-Glaucine
(S)-configuration 		(R)-Glaucine
(R)-configuration

Mechanism of action

Glaucine binds to the

L-type Ca2+-channels, thereby blocking calcium ion channels in smooth muscle like the human bronchus. Glaucine has no effect on intracellular calcium stores, but rather, does not allow the entry of Ca2+ after intracellular stores have been depleted.[6] Ca2+ influx is a vital component in the process of muscular contraction, and the blocking of this influx therefore reduces the ability of the muscle to contract.[14]
In this way, glaucine can prevent smooth muscle from contracting, allowing it to relax.

Glaucine has also been demonstrated to be a

PDE4 inhibitor, glaucine possesses very low potency.[6]

Glaucine has also recently

psychedelics. It also inhibits MAO enzymes.[16] Its enantiomers effect are same for adrenergic receptor yet different for 5-HT receptor. Both (R)-Glaucine and (S)-Glaucine antagonizes α1 receptor but (S)-Glaucine is partial agonist of 5-HT2 subtypes whereas (R)-Glaucine is positive allosteric modulator of 5-HT2.[17]

Uses

Medical

It is currently used as an

antitussive agent in Iceland, as well as Romania, Bulgaria, Russia and other eastern European countries.[6][11] Bulgarian pharmaceutical company Sopharma sells glaucine in tablet form, where a single dose contains 40 mg and the half-life is indicated to be 6–8 hours. When ingested orally has been shown to increase airway conductance in humans, and has been investigated as a treatment for asthma.[6]

Glaucine has been reported to reduce blood pressure, heart rate and possess anticonvulsant and antinoiciceptive effect in animals[18][19]

Recreational

Reports of recreational use of glaucine have recently been published, and effects include dissociative-type symptoms; feeling detached and 'in another world', as well as nausea, vomiting and dilated pupils. These reports mirror those about the effects of clinical use, which state dissociative-type symptoms as well as lethargy, fatigue, hallucinations.[10][11] Investigation of side effects in a clinical setting also reports that the hallucinatory effects manifest as bright and colorful visualizations. They also report that patients perceive their environments clearly yet feel detached from it; "the patient sees and understands everything and is oriented well enough, but cannot take a clear and adequate action".[10]

One particular report of recreational use gone awry described the form of distribution as tablets being marketed as a 1-benzylpiperazine (BZP)-free "herbal high" which the patient referred to as "head candy".[11]

See also

References

  1. S2CID 44040818
    . S-(+)-Glaucine (C21H25NO4) is the main alkaloid component in the grass of yellow horn poppy (Glaucium luteum L., syn. Glaucium flavum Crantz) of the family Papaveraceae
  2. PMID 15706885
    .
  3. PMID 12837370
    .
  4. PMID 12088421
    .
  5. PMID 2907279
    .
  6. ^
    PMID 10455321
    .
  7. PMID 6375709
    .
  8. PMID 19481591
    .
  9. PMID 2586025
    .
  10. ^
    PMID 17243616
    .
  11. ^
    S2CID 21348503
    .
  12. ^ a b Heng, HL, Chee, CF, Thy, CK, et al. In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5‐HT2 and α1 receptors. Chem Biol Drug Des. 2019; 93: 132– 138. https://doi.org/10.1111/cbdd.13390
  13. PMID 35672295
    .
  14. ^ Nestler E, Hyman S & Malenka R. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). China: McGraw-Hill Companies.
  15. PMID 15862999
    .
  16. S2CID 73448412
    .
  17. S2CID 52278437
    .
  18. PMID 2907279
    .
  19. PMID 7606346
    .
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