25i - nbome

Discussie in 'Psychodelics' gestart door Charles Darwin, 2 mei 2014.

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    Charles Darwin

    Charles Darwin Guest

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    25I-NBOMe(2C-I-NBOMe,Cimbi-5)

    is a
    and derivative of the
    psychedelic
    . It was discovered in 2003 by chemist Ralf Heim at the
    , who published his findings in his PhD dissertation. The compound was subsequently investigated by a team at
    led by
    .

    The carbon-11 labelled version of 25I-NBOMe,[11C]Cimbi-5, was synthesized and validated as a
    for
    (PET) in Copenhagen. Being the first 5-HT2Areceptor full agonist PET radioligand,[11C]Cimbi-5 shows promise as a more functional marker of these receptors.

    Chemistry and structure

    Like other 2C-X-NBOMe molecules, 25I-NBOMe is a derivative of the
    family of phenethylamines described by
    in his book
    . SpecifiCally, 25I-NBOMe is anN-benzyl derivative of the phenethylamine molecule
    , formed by adding a 2-methoxybenzyl (MeOB) onto the nitrogen (N) of the phenethylamine backbone. This substitution significantly increases the potency of the molecule.

    Synthesis

    25I-NBOMe is usually synthesised from 2C-I and 2-methoxybenzaldehyde, via reductive
    . It can be done stepwise by first making the
    and then
    the formed imine with
    , or by direct reaction with
    .

    Pharmacology

    Ki-values
    ReceptorKi (nM)±
    0.044
    2
    7312
    8214
    18935
    23173
    28850

    25I-NBOMe acts as a highly
    full
    for the
    , with a
    of 0.044 nM, making it some sixteen times the potency of 2C-I itself, and a
    form of 25I-NBOMe can be used for mapping the distribution of 5-HT2Areceptors in the brain. It is one of the only full
    of the
    in existence.
    tests showed this compound acted as an agonist. Head twitch studies in mice have confirmed that 25I-NBOMe activates the
    receptor in vivo, and demonstrated that 25I-NBOMe is approximately 14-fold more potent than 2C-I. While the in vitro studies showed thatN-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, theN-benzyl derivatives of
    were inactive.

    Ki values of the following targets were greater than 500 nM:
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    ,
    , and the
    .

    A forensic standard of 25I-NBOMe is available, and the compound has been posted on the Forendex website of potential drugs of abuse.

    25I-NBOMe induces a
    in mice which is blocked completely by a selective 5-HT2Aantagonist, suggesting its psychedelic effects are mediated by 5-HT2A.

    Recreational use

    Although 25I-NBOMe was discovered in 2003, it did not emerge as a common recreational drug until 2010, when it was first sold by vendors specialising in the supply of
    . In a slang context, the name of the compound is often shortened to “25I”. According to a 2014 survery, 25I-NBOMe is the most frequently used of the NBOMe series. Case reports of 25I-NBOMe intoxication, with and without analytic confirmation of the drug in the body, are increasing in the medical literature.

    25I-NBOMe is inactive orally, and the most common methods of administration are sublingual,
    , and nasal. For sublingual and buccal administration, 25I-NBOMe is applied to sheets of blotter paper — usually perforated with a uniform grid — of which small portions (tabs) are placed under the tongue or in the buccal space of the mouth, where the drug can be readily absorbed via mucous membranes. There are reports of intravenous injection of 25I-NBOMe solution and smoking the drug in powdered form.

    Due to its potency, small quantities of 25I-NBOMe can provide a large numbers of doses. Vendors may import 25I-NBOMe in bulk and resell individual doses for considerable profit.

    Because blotter paper is also a common distribution medium for
    , 25I-NBOMe blotters are sometimes misrepresented as, and mistaken for, LSD blotters. It is dangerous to attempt to differentiate the two using
    techniques (i.e. taste) but
    (particularly
    ) can be used to easily differentiate
    from 25-I NBOMe by a colour change.

    Dosage

    25I-NBOMe is potent, being active in sub-milligram doses. A common dose of the hydrochloride salt is 600–1,200
    . The UK Advisory Council on the Misuse of Drugs states that a common dose is between 50 and 100 µg,
    although other sources indicate that these figures are incorrect;
    tentatively suggests that the threshold dosage for humans is 50–250 µg, with a light dose between 200–600 µg, a common dose at 500–800 µg, and a strong dose at 700–1500 µg.
    At this level of potency, it is not possible to accurately measure a single dose of 25I-NBOMe powder without an analytical balance, and attempting to do so may put the user at significant risk of overdose.

    Effects

    25I-NBOMe effects usually last 6–10 hours if taken sublingually or bucCally. When it is insufflated, effects usually last 4–6 hours. Effects can however last significantly longer depending on dosage; durations longer than 12 hours have been reported.

    25I-NBOMe can also be vaporized and inhaled, this may cause significantly quicker effects and shorter duration as is expected from that route of administration. This route of administration is however not recommended, unless when using precise liquid measurement, due to the difficulties of measuring and handling substances active in the microgram range.

    25I-NBOMe has similar effects to LSD, though users report more negative effects while high and more risk of harm following use as compared to other classic psychedelics.

    Case reports of seven British males who presented to an emergency room following analytiCally confirmed 25I-NBOMe intoxication suggest the following potential adverse effects:tachycardia (n = 7), hypertension (4), agitation (6), aggression, visual and auditory hallucinations (6), seizures (3), hyperpyrexia (3), clonus (2), elevated white cell count (2), elevated creatine kinase (7), metabolic acidosis (3), and acute kidney injury (1).
     
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    Charles Darwin, 2 mei 2014
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