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Havidol (Hopefully the only fake molecule of the day I'll ever do)

By moleculeoftheday on February 20, 2007.

See also the followups (one, two) to this post.

From the taking jokes too seriously department...

Havidol is a fake drug campaign by Justine Cooper that's on display in NY at the Daneyal Mahmood gallery (warning, slow loading, natively embedded video). It seems like a pretty well-done faux-drug site, and the gist seems to be mocking the idea that "lifestyle drugs" are becoming more and more ubiquitous.

I could go on about on the social aspects of this kind of drug and this kind of commentary, but that's not what I'm aiming for. (Besides, plenty of people are on that; even Reuters covered it.) I write about structures. What's the problem with Havidol? They're more than a little off on their chemistry.

From the "prescribing information" (PDF):

HAVIDOL® (avafynetyme HCl), an oral or anal treatment for dysphoric social attention consumption deficit anxiety disorder, is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).

avafynetyme HCl has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The
structural formula is:

i-5e1565cc281520246322f786ce3e5c13-havidol.gif

(subtitles mine, structure recreated manually from PDF)

The chemical designation is pyrazino[1?,2?:1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-
2,3,6,7,12,12a-hexahydro-2-methyl-,(6R,12aR)-. (sic)

The given structure has empirical (more appropriately, molecular) formula C21H18O2. No nitrogens, not a hydrochloride salt, certainly posessing miserable solubility, and PDE5 isn't probably the target you're after for "DSACDAD." The molecular weight is 302.37, not 389.41. The nomenclature also doesn't match; the true nomenclature for the structure illustrated in the PDF is given in the graphic above.

The IUPAC-type nomenclature given looks like an obfuscated version of that of Cialis. A molecular formula of C22H19N3O4 and molecular weight of 389.41 match as well. Here is Cialis, along with its (correct) nomenclature:

i-aded8195f7cf7c515e736a0029f85b86-cialis.gif

Different, no?

I know it's a joke, I get the point, and I know that a tiny fraction of people noticed or cared. However, artists: consider consulting a chemist before you do a parody that relies on chemistry.

See also commentary from Mind Hacks and Boing Boing.

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Scientists can undetectably fake being Liberal Artists (re Alan Sokol, anthropogenic Global Waring) but the reverse does not obtain. Objective truth can be artsy but not arsty-fartsy.

Let's all stop taking our Ephemerol and then do it the Scanners way.

Wouldn't having an empirical formula that didn't match the structure add to the absurdity of it all, showing just how little people really do pay attention to (a) when they need medications and (b) what their medications actually are? I would actually think that is quite intentional, and you are splitting hairs on something that is clearly meant to be absurd in every way...

From the Cialis prescribing information (PDF):

CIALIS� (tadalafil), an oral treatment for erectile dysfunction, is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The structural formula is:

(image, redacted)

The chemical designation is pyrazino[1â²,2â²:1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-
benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-. It is a crystalline solid that is practically insoluble in water and very slightly soluble in ethanol.
CIALIS is available as film-coated, almond-shaped tablets for oral administration. Each tablet contains 5, 10, or 20 mg of tadalafil and the following inactive ingredients: croscarmellose sodium, hydroxypropyl cellulose, hypromellose, iron oxide, lactose monohydrate, magnesium stearate, microcrystalline cellulose, sodium lauryl sulfate, talc, titanium dioxide, and triacetin.

Pretty similar to that for Havidol.

BobC:

The chemical mismatch is incongruous with the rest of the parody. The parody is very careful to be specific (cGMP-specific phosphodiesterase) or completely make something up (the molecule, the target). No, it's more likely due to being a lazy artist. These days, in the art community, intent is more important than technique anyway.

Darksyde- Actually, take a look at the PDFs. Large portions of the prescribing info for "havidol" match with the cialis monograph. This seems to be where references to PDE5 come from.

Her glossary page appears to be quite similar to that found on the Lexapro website, as well. From the Havidol site:

Also known as side effects, adverse events are the secondary, usually negative, effects caused by medicine. They are recorded as the percentage of patients who experience the adverse event. For example, if 10 people out of 100 in a clinical trial take a medicine and develop a headache, then 10% of the study participants experienced this adverse event. A well-tolerated medicine is associated with low rates of adverse events.

From the Lexapro site:

Also known as side effects, adverse events are the secondary, usually negative, effects caused by medicine. They are recorded as the percentage of patients who experience the adverse event. For example, if 10 people out of 100 in a clinical trial take a medicine and develop a headache, then 10% of the study participants experienced this adverse event. A well-tolerated medicine is associated with low rates of adverse events.

Ironically, the legal and privacy pages look similar to some out there, but there is a lot of similarity between sites on these...

I stand corrected (wrt PDE5) but I think your observation buttresses my point.

We at HAVIDOL are flattered that you have thought to include us in your blog.
A kind professor of chemistry had advised us of the errors of our ways a few days ago. We have endeavored to make some changes to the PI on the HAVIDOL site. But we are just a bunch of lazy artists over here so it has been quite difficult to implement these changes and we are quite sure we have probably bungled it anyway. Our original chemistry specialist was discredited when it turned out that he was acutally a veterinary pathologist and not a chemist at all!
We'd like to send a HAVIDOL T-shirt ($25 value) to anyone out there interested in concocting an authentic HAVIDOL Prescribing Information PDF. It's only 25 pages long and at a $1/page that is more than any of us have been paid since we took on this god-forsaken job of constructive parody.
Bob C. had a point when he said that most people never notice anyway. So it is our privilege to be 'exposed' by molecule of the day. Certainly the ad people who came to the physical exhibition never noticed.
Thanks for making us feel special.
The HAVIDOL team.