Cathine

Last updated
D-norpseudoephedrine
Cathine2DCSD.svg
Cathine3DanJ.gif
Clinical data
Other names
  • (+)-norpseudoephedrine
  • Cathine
Routes of
administration
Oral
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 1.8–8.6 hours [1]
Identifiers
  • (1S,2S)-2-amino-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.050 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H13NO
Molar mass 151.209 g·mol−1
3D model (JSmol)
Solubility in water 20 mg/mL (20 °C)
  • O[C@@H](c1ccccc1)[C@@H](N)C
  • InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1 Yes check.svgY
  • Key:DLNKOYKMWOXYQA-IONNQARKSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

D-norpseudoephedrine, also known as cathine and (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant. Along with cathinone, it is found naturally in Catha edulis (khat), and contributes to its overall effects. [2] It has approximately 7-10% the potency of amphetamine. [2]

Contents

Pharmacology

Like amphetamines, cathinone and ephedrine, cathine acts as a norepinephrine releasing agent (NRA). [2] It also acts as a dopamine releasing agent (DRA). [2] [3]

Chemistry

Cathine is one of the four stereoisomers of phenylpropanolamine (PPA).

Regulation

The World Anti-Doping Agency's list of prohibited substances (used for the Olympic Games among other athletic events) bars cathine in concentrations of over 5 micrograms per milliliter in urine. Cathine is a Schedule III drug under the Convention on Psychotropic Substances. [4] In the United States, it is classified as a Schedule IV controlled substance. [5]

In Australia, Cathine is officially a schedule 4 drug prescription only, but is not available or approved for any medical use.

Cathine is found in the shrub khat (Catha edulis). Catha edulis.jpg
Cathine is found in the shrub khat ( Catha edulis ).

In Hong Kong, cathine is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. Unlawful possession is punishable by severe fines and imprisonment.

Pregnancy

Ephedra, found in many Ephedraceae species, is a Chinese and Western herb that contains, among other amphetamines, D-norpseudoephedrine. In the National Birth Defects Prevention Study, which included 18,438 women from 10 states from 1999 to 2003, 1.3% of women reported using ephedra during pregnancy. During the trial, five cases of anencephaly were born to women who used ephedra, however there was no statistically significant association to women not using ephedra (odds ratio 2.8, confidence interval 1.0–7.3). [6]

A small study of 642 participants in Yemen found that among pregnant women who chewed khat (containing D-norpseudoephedrine) there was no increased risk of stillbirth or congenital malformations. [7] Among lactating women who chew khat, D-norpseudoephedrine is found in breastmilk. [8]

See also

Related Research Articles

<span class="mw-page-title-main">Amphetamine</span> Central nervous system stimulant

Amphetamine is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

<span class="mw-page-title-main">Khat</span> Species of plant, commonly used for its psychoactive effects

Khat or qat is a flowering plant native to eastern and southern Africa. Khat contains the alkaloid cathinone, a stimulant, which is said to cause excitement, loss of appetite, and euphoria. Among communities from the areas where the plant is native, khat chewing has a history as a social custom dating back thousands of years analogous to the use of coca leaves in South America and betel nut in Asia.

<span class="mw-page-title-main">Stimulant</span> Overarching term covers many drugs that increase activity of the central nervous system

Stimulants is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and invigorating, or drugs that have sympathomimetic effects. Stimulants are widely used throughout the world as prescription medicines as well as without a prescription as performance-enhancing or recreational drugs. Among narcotics, stimulants produce a noticeable crash or comedown at the end of their effects. The most frequently prescribed stimulants as of 2013 were lisdexamfetamine (Vyvanse), methylphenidate (Ritalin), and amphetamine (Adderall). It was estimated in 2015 that the percentage of the world population that had used cocaine during a year was 0.4%. For the category "amphetamines and prescription stimulants" the value was 0.7%, and for MDMA 0.4%.

<span class="mw-page-title-main">Ephedrine</span> Medication and stimulant

Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.

<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.

Stimulant psychosis is a mental disorder characterized by psychotic symptoms which involves and typically occurs following an overdose or several day 'binge' on psychostimulants; however, it has also been reported to occur in approximately 0.1% of individuals, within the first several weeks after starting amphetamine or methylphenidate therapy. Methamphetamine psychosis, or long-term effects of stimulant use in the brain, depend upon genetics and may persist for some time.

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

Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs.

<span class="mw-page-title-main">Sympathomimetic drug</span> Substance that mimics stimulation of catecholaminergic receptors

Sympathomimetic drugs are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in heart rate, force of cardiac contraction, and blood pressure. The primary endogenous agonists of the sympathetic nervous system are the catecholamines, which function as both neurotransmitters and hormones. Sympathomimetic drugs are used to treat cardiac arrest and low blood pressure, or even delay premature labor, among other things.

<span class="mw-page-title-main">Phentermine</span> Weight loss medication

Phentermine (phenyl-tertiary-butylamine), with several brand names including Ionamin and Sentis, is a medication used together with diet and exercise to treat obesity. It is taken by mouth for up to a few weeks at a time, after which the beneficial effects no longer occur. It is also available as the combination phentermine/topiramate.

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

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

<span class="mw-page-title-main">Lisdexamfetamine</span> CNS stimulant (prodrug)

Lisdexamfetamine, sold under the brand name Vyvanse among others, is a stimulant medication that is mainly used to treat attention deficit hyperactivity disorder (ADHD) in people over the age of five as well as moderate-to-severe binge eating disorder in adults. Lisdexamfetamine is taken by mouth. Its effects generally begin within 2 hours and last for up to 14 hours. In the United Kingdom, it is usually less preferred than methylphenidate for the treatment of children.

<span class="mw-page-title-main">Convention on Psychotropic Substances</span> 1971 UN treaty to regulate recreational drugs

The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February 1971. The Single Convention on Narcotic Drugs of 1961 did not ban the many newly discovered psychotropics, since its scope was limited to drugs with cannabis, coca and opium-like effects.

<span class="mw-page-title-main">Norepinephrine releasing agent</span> Catecholaminergic type of drug

A norepinephrine releasing agent (NRA), also known as an adrenergic releasing agent, is a catecholaminergic type of drug that induces the release of norepinephrine (noradrenaline) and epinephrine (adrenaline) from the pre-synaptic neuron into the synapse. This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine therefore an increase in adrenergic neurotransmission.

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, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-Norpseudoephedrine Chemical compound

L-Norpseudoephedrine, or (−)-norpseudoephedrine, is a psychostimulant drug of the amphetamine family. It is one of the four optical isomers of phenylpropanolamine, the other three being cathine ((+)-norpseudoephedrine), (−)-norephedrine, and (+)-norephedrine; as well as one of the two enantiomers of norpseudoephedrine (the other being cathine). Similarly to cathine, L-norpseudoephedrine acts as a releasing agent of norepinephrine (EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM). Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, L-norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine.

Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be mislabeled as plant food, powdered cleaner, and other such products.

<i>N</i>-Ethylhexedrone Chemical compound

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

References

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  2. 1 2 3 4 Hoffman R, Al'Absi M (December 2010). "Khat use and neurobehavioral functions: suggestions for future studies". Journal of Ethnopharmacology. 132 (3): 554–63. doi:10.1016/j.jep.2010.05.033. PMC   2976806 . PMID   20553832.
  3. Kalyanasundar B, Perez CI, Arroyo B, Moreno MG, Gutierrez R (2020-10-16). "The Appetite Suppressant D-norpseudoephedrine (Cathine) Acts via D1/D2-Like Dopamine Receptors in the Nucleus Accumbens Shell". Frontiers in Neuroscience. 14: 572328. doi: 10.3389/fnins.2020.572328 . PMC   7596745 . PMID   33177980.
  4. "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 2012-08-31.
  5. "Scheduling Actions" (PDF). Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA).
  6. Smid MC, Metz TD, Gordon AJ (March 2019). "Stimulant Use in Pregnancy: An Under-recognized Epidemic Among Pregnant Women". Clinical Obstetrics and Gynecology. 62 (1): 168–184. doi:10.1097/GRF.0000000000000418. PMC   6438363 . PMID   30601144.
  7. Nakajima M, Jebena MG, Taha M, Tesfaye M, Gudina E, Lemieux A, et al. (October 2017). "Correlates of khat use during pregnancy: A cross-sectional study". Addictive Behaviors. 73: 178–184. doi:10.1016/j.addbeh.2017.05.008. PMID   28531823.
  8. Kristiansson B, Abdul Ghani N, Eriksson M, Garle M, Qirbi A (September 1987). "Use of khat in lactating women: a pilot study on breast-milk secretion". Journal of Ethnopharmacology. 21 (1): 85–90. doi:10.1016/0378-8741(87)90097-3. PMID   3695559.