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Science Alert: Experts Respond

‘Legal high’ DIME not so legal

Posted in Science Alert: Experts Respond on March 13th, 2012.

The DIME logo and a photo of DIME capsules from the dime.co.nz website

The active ingredient in a supposedly legal party drug sold in New Zealand has been revealed to be a Class C controlled substance.

An analysis undertaken by the Crown Research Institute ESR, commissioned by TVNZ, indicated that the “party drug” product DIME contains the new drug 25C-NBOMe (also known as Pandora or Cimbi 82), which has been reported to be an hallucinogen nearly as potent as LSD.

The DIME website (now shut down) described the drug:

“…snorting the substance will bring on an amazing high, increased energy, and beautiful visuals, while not being too trippy to render you useless of socialization. An amazing mood amplifier for any situation.”

The ESR drugs laboratory has determined that 25C-NBOMe is an analogue – a slightly altered version – of the Class A controlled drug DOB (aka Bromo-DMA) and is therefore a Class C drug under the Misuse of Drugs Act controlled drug analogue “safety net” clause (Misuse of Drugs Act 1975, Section 2(1)).

25C-NBOMe appears to have been first synthesised in 2009 and was reported last year in the scientific literature.

The Science Media Centre collected the following commentary from experts. Feel free to use these quotes in your reporting. If you would like to contact a New Zealand expert, please contact the SMC (04 499 5476; smc@sciencemediacentre.co.nz).

Dr Paul Fitzmaurice, Bioanalytical Programme Manager, ESR, comments:

“A sample of DIME was tested in our drugs lab in Auckland where they performed a GCMS analysis of the sample. They got a result which indicated a similarity to substances we had seen before but, not an absolute match. Going back to basic chemical theory, we were able elucidate what the structure might be. Fortunately, we also have link into a network of labs that operate internationally to share information on emerging drugs and we saw information from a German lab that had seen the same product. That allowed us to give a match to the product – 25C-NBOMe”

“The supplier claims that there are 150 micrograms are in each capsule, which is in the same dosage range as LSD.

“I think the supplier of DIME had been looking at the Misuse of Drugs Act, which gives examples of what an analogue might be. According to those examples he was determining that 25C-NBOMe was not a controlled substance analogue – and according to those examples it isn’t. But there is also a quite general clause in the act which states that an analogue is any compound “substantially similar” to a controlled substance. On those terms our drugs lab determined that the base structure for 25C-NBOMe is basically DOB- a Class A substance.

“If you were looking at it in its own right, 25C-NBOMe should probably be a Class A drug [all analogues are automatically Class C].

“My advice to anyone thinking about taking these products: don’t. There is very little published literature and little or no information about dosage or consequences.”

Dr Leo Schep, Toxicologist, National Poisons Center, comments:

“The drug 25C-NBOMe (Dime) is a derivative of the psychoactive drug called 2C-C (4-chloro-2,5-dimethoxy-phenethylamine), which itself is part of a group of modified phenethylamine (amphetamine-like) structures called dimethoxyphenyl-ethanamines; they are also known as 2- C substitutes.

“This group of modified amphetamines typically confer hallucinogenic activity due to modifications of the aromatic ring with methoxy substitutes at the 2 and 5 position plus a hydrophobic substitution (typically though, not always, a halide) at position 4. They act as serotonin receptor agonists, particularly at the 5HT2a receptors, notably in the cerebral cortex.

“Stimulation at these sites can evoke hallucinations but there is also the added risk of paranoia and schizophrenia, as has been documented in some case reports.

“The molecule does possess hallucinogenic activity, but this is poor when compared with other like-substitutes and LSD.”

Dr Anders Ettrup, Post-doctoral researcher, Neurobiology Research Unit, Copenhagen University Hospital, Denmark, has worked closely with 25C-NBOMe (Cimbi-82) in a research setting. He comments:

“To my knowledge, we (Ettrup et al. 2011) were the first to report the synthesis of the chemical that we call Cimbi-82 in the scientific literature. This was to test this potential to be used as a chemical for imaging the status of the serotonin system in animals. We hypothesize that such research will yield important insights into the pathophysiology of human disease such as depression. However, whether or not this synthesis previously has been described in the ‘less scientific’ literature, I don’t know.

“All the compounds investigated in the 2011 report are highly potent and act in a similar way to LSD. The hallucinogenic effect of these compounds (such as LSD) is attributed to their activation of 5-HT2A receptors.

“To my knowledge, Cimbi-82 has not been given in controlled animal studies or been administered to humans in a controlled fashion!”

Dr Martin Hansen, Department of Drug Design & Pharmacology, University of Copenhagen is a colleague of Dr Ettrup. He comments:

“We were the first to report the synthesis and pharmacology of 25C-NBOMe (2C-C-NBOMe, Cimbi-82). We submitted it for pharmacological testing in July 2009 so it was first synthesized somewhere between March 2009 and July 2009.

“It wouldn’t take much effort to deduce that 25C-NBOMe would be an active hallucinogen, since the closely related compounds 25I-NBOMe, 25B-NBOMe and 25TFM-NBOMe were reported as potent 5-HT2A agonists as early as 2003 by Ralf Heim. Therefore I cannot exclude the possibility that it was first made by some clever  clandestine chemists before March 2009.

“We initiated our research into these compounds by investigating 25I-NBOMe (Cimbi-5), a known compound, as a potential radiotracer and then progressed via subtle modifications of the molecule to improve it’s suitability as a radiotracer, in this process we also tested 25C-NBOMe, but it didn’t provide any improvement over previous compounds so we left it there.

“There has been no human research into the effects of 25C-NBOMe.

“25C-NBOMe is a very potent compound, though not quite as potent as LSD. One of my main concerns with this compound (and the other NBOMe-compounds) is that, unlike LSD, they are not absorbed in the gut. They are instead administered intranasally or sublingually which presents a greater risk of overdosing because some of the dose may accidentally be swallowed (and thus rendered inactive) at one time and not at other times, leading to some very inconsistent dosage reports. With a compound that is potentially active at 500 mcg, there is a not a lot of margin for error.

“It is less than a month ago that 25I-NBOMe [a similar compound] made breaking news in Richmond, VA, with several overdose reports which just serves to underline that these compounds are not toys.”

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