Vasicinone

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Vasicinone
Vasicinone.svg
Names
Preferred IUPAC name
(1S)-1-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-5(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.620 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1
    Key: SDIVYZXRQHWCKF-VIFPVBQESA-N
  • C1CN2C(=NC3=CC=CC=C3C2=O)[C@H]1O
Properties
C11H10N2O2
Molar mass 202.213 g·mol−1
Density 1.5 g/cm3
Melting point 200 to 202 °C (392 to 396 °F; 473 to 475 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vasicinone is a quinazoline alkaloid. It shows bronchodilator action in vitro [1] but bronchoconstrictor action in vivo. [2] Vasicinone was shown to have an antianaphylactic action. [3] It has been found within Peganum harmala . [4]

Vasicinone has also been studied in combination with the related alkaloid vasicine. Both the alkaloids in combination (1:1) showed pronounced bronchodilatory activity in vivo and in vitro. [5] Both alkaloids are also respiratory stimulants. [5] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids. [5] [3] Vasicine is reported to have a uterine stimulant effect. [3]

Related Research Articles

<span class="mw-page-title-main">Xanthine</span> Chemical compound

Xanthine is a purine base found in most human body tissues and fluids, as well as in other organisms. Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.

<i>Banisteriopsis caapi</i> Species of plant

Banisteriopsis caapi, also known as, caapi, soul vine, or yagé (yage), is a South American liana of the family Malpighiaceae. It is commonly used as an ingredient of ayahuasca, a decoction with a long history of its entheogenic use and its status as a "plant teacher" among the Indigenous peoples of the Amazon rainforest.

β-Carboline Chemical compound also known as norharmane

β-Carboline (9H-pyrido[3,4-b]indole) represents the basic chemical structure for more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant effects. Synthetically designed β-carboline derivatives have recently been shown to have neuroprotective, cognitive enhancing and anti-cancer properties.

<span class="mw-page-title-main">Harmala alkaloid</span> Group of chemical compounds

Harmala alkaloids are several alkaloids that increase effects of reward system neurotransmitter dopamine by acting as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of Peganum harmala, as well as leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

<i>Peganum harmala</i> Species of plant

Peganum harmala, commonly called wild rue, Syrian rue, African rue, esfand or espand, or harmel, is a perennial, herbaceous plant, with a woody underground rootstock, of the family Nitrariaceae, usually growing in saline soils in temperate desert and Mediterranean regions. Its common English-language name came about because of a resemblance to rue. Because eating it would sicken or kill livestock, it is considered a noxious weed in a number of countries. It has become an invasive species in some regions of the western United States. The plant is popular in Middle Eastern and north African folk medicine. The alkaloids contained in the plant, including the seeds, are monoamine oxidase inhibitors.

Harmine is a beta-carboline and a harmala alkaloid. It occurs in a number of different plants, most notably the Syrian rue and Banisteriopsis caapi. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a Reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B. Harmine is also known as banisterin, banisterine, telopathin, telepathine, leucoharmine and yagin, yageine.

<span class="mw-page-title-main">Harmaline</span> Chemical compound

Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.

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<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

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<i>Justicia adhatoda</i> Species of flowering plant

Justicia adhatoda commonly known in English as Malabar nut, adulsa, adhatoda, vasa, vasaka, is native to Asia.

<span class="mw-page-title-main">Tetrahydroharman</span> Chemical compound

Tetrahydroharman(e), also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a general name for one of two isomers:

  1. (1S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  2. Calligonine ((1R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole)
<span class="mw-page-title-main">Glaucine</span> Chemical compound

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, Glaucium oxylobum and Corydalis yanhusuo, and in other plants like Croton lechleri in the family Euphorbiaceae.

<span class="mw-page-title-main">Higenamine</span> Chemical compound

Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum, Annona squamosa, and Nelumbo nucifera.

<i>Cissus quadrangularis</i> Species of grapevine

Cissus quadrangularis is a perennial plant of the grape family. It is commonly known as veldt grape, winged treebine or adamant creeper. The species is native to tropical Asia, the Arabian Peninsula and much of Africa.

<span class="mw-page-title-main">Harmane</span> Chemical compound

Harmane (harman) is a heterocyclic amine found in a variety of foods including coffee, sauces, and cooked meat. It is also present in tobacco smoke.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">Palmatine</span> Chemical compound

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis and Corydalis yanhusuo, Tinospora cordifolia, Tinospora sagittata, Phellodendron amurense, Stephania yunnanensis.

<span class="mw-page-title-main">Vasicine</span> Chemical compound

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda, after which it is named. It is additionally found in Peganum harmala.

<span class="mw-page-title-main">Quinazoline alkaloids</span>

Quinazoline alkaloids are natural products from the group of alkaloids, which are chemically derived from quinazoline. Some quinazoline alkaloids show bronchodilatory effects and stimulate respiration. An abortive effect was also found for vasicine in studies on rats and rabbits.

References

  1. Amin, A. H.; Mehta, D. R. (1959). "A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees". Nature. 184 (4695): 1317. Bibcode:1959Natur.184.1317A. doi: 10.1038/1841317a0 . ISSN   0028-0836. PMID   13793186.
  2. Mehta, D. R.; Naravane, J. S.; Desai, R. M. (1963). "Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae)". The Journal of Organic Chemistry. 28 (2): 445–448. doi:10.1021/jo01037a041. ISSN   0022-3263.
  3. 1 2 3 Rajani, M; Soni, S; Anandjiwala, Sheetal; Patel, G (2008). "Validation of different methods of preparation of Adhatoda vasica leaf juice by quantification of total alkaloids and vasicine". Indian Journal of Pharmaceutical Sciences. 70 (1): 36–42. doi: 10.4103/0250-474X.40329 . ISSN   0250-474X. PMC   2852058 . PMID   20390078.
  4. Moloudizargari M, Mikaili P, Aghajanshakeri S, Asghari MH, Shayegh J (July 2013). "Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids". Pharmacogn Rev. 7 (14): 199–212. doi: 10.4103/0973-7847.120524 . PMC   3841998 . PMID   24347928.
  5. 1 2 3 Avula, B.; et al. (2008). "Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis" (PDF). Die Pharmazie. 63 (1): 20–22. doi:10.1691/ph.2008.7175. PMID   18271297.