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Old 11-06-2008, 10:02 PM   #1
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Default Tobacco Road!

I am thinking of building a Bourbon barrel porter, but with a twist. I'm thinking of sticking a few maduro wrapper cigars in the secondary with the oak. I don't' think that I'll do it, because I really don't want people getting a nicotine buzz from my beer. I did see the Pipe Tobacco thread, and I guess more what I ask...knowing what I know about Nicotine, is how to make tobacco flavor, without using tobacco. But I do think that the tobacco flavors would compliment the beer.
Thoughts?

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Old 11-06-2008, 10:13 PM   #2
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I often hear tobacco as a descriptor in Old Ales, Barleywines, and Imperial Stouts. I am very interested in how to duplicate these flavors. I suspect that oak cubes, of the right toast, could impart it?

...is Nicotine alcohol-soluble?

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Old 11-06-2008, 10:13 PM   #3
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I think that would be really nice if one could create that flavor. With the right malts and amounts i have had beers were there is a slight tobacco flavor but no idea what the grist was made up of.

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Old 11-06-2008, 10:22 PM   #4
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Quote:
Originally Posted by Chriso View Post
...is Nicotine alcohol-soluble?
Hah, I dunno.

I'm sure you could extract it somehow, might take a bit more work though. Maybe butane?

I would avoid leaving tobacco in contact with it for long, the taste sounds like it could work but it'd be hard to get it just right IMO.
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Old 11-06-2008, 10:30 PM   #5
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Quote:
Taste:
A very smooth vanilla start leads to an organic dark fruit or dank farmhouse fruit middle that is reminiscent of plum, fig, and raisin. The middle also showcases a complex and subtly sweet smoke flavor that is detectable but not overpowering. The finish is nicely hopped but also brings a chocolaty oat flavor. Just before the hopped finish a rich wet maduro tobacco flavor shines through. After taste leaves a fresh hay note that is very pleasing and mellow.
These were the tasting notes from my Smokey Boggart. The tobacco flavor was nice and subtle. No tobacco was used and it definitely wasn't the driving flavor, but it was there.
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Old 11-07-2008, 03:16 AM   #6
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Quote:
Originally Posted by Kilgore_Trout View Post
I'm sure you could extract it somehow, might take a bit more work though. Maybe butane?
Ah- I was referring to *not* extracting the nicotine (God knows I have a big enough problem with the crap already) and just imparting the taste/sensory perception of the tobacco.
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Old 11-07-2008, 03:31 AM   #7
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I don't think it's advisable to put cigars into your beer. Nicotine is HIGHLY toxic, and it is indeed miscible with water (it's an oil, so it isn't water soluble, but it will mix with water, unlike petroleum based oils). I remember reading a "recipe" to deliberately concentrate nicotine for use as a poison. Supposedly a single can of dip contains enough to provide a lethal dose.

I can't really provide any sources (mostly because I don't remember where I read this crap), so you'll have to chalk this post up to "hearsay." However, I doubt there's a way to dunk cigars in your beer without extracting at least some nicotine, so I think you'll need to find another means of achieving tobacco flavor.

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Old 11-07-2008, 05:25 AM   #8
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Straight from the Merck Index!

Quote:
Monograph Number: 6551
Title: Nicotine
CAS Registry Number: 54-11-5
CAS Name: 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine
Additional Names: 1-methyl-2-(3-pyridyl)pyrrolidine; b-pyridyl-a-N-methylpyrrolidine
Trademarks: Habitrol (Novartis); Nicabate (HMR); Nicoderm CQ (SKB); Nicolan (Elan); Nicopatch (Fabre); Nicotinell (Novartis); Tabazur (Théraplix)
Molecular Formula: C10H14N2
Molecular Weight: 162.23.
Percent Composition: C 74.04%, H 8.70%, N 17.27%
Literature References: From the dried leaves of Nicotiana tabacum and N. rustica where it occurs to the extent of 2 to 8%, combined with citric and malic acids. Extraction procedure: Gattermann, Wieland, Laboratory Methods of Organic Chemistry (New York, 24th ed., 1937); Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931). Purification: Ratz, Monatsh. 26, 1241 (1905). Structure and synthesis: Pinner, Ber. 26, 294 (1893); Pictet, Rotschy, Ber. 37, 1225 (1904); Craig, J. Am. Chem. Soc. 55, 2854 (1933); M. Nakane, C. R. Hutchinson, J. Org. Chem. 43, 3922 (1978). Conformation in soln: T. P. Pitner et al., J. Am. Chem. Soc. 100, 246 (1978). HPLC determn in plasma: M. Harlharan et al., Clin. Chem. 34, 724 (1988). Toxicity data: R. B. Barlow, L. J. McLeod, Brit. J. Pharmacol. 35, 161 (1969). Review and bibliography: Jackson, Chem. Rev. 29, 123 (1941). Review of pharmacology: R. W. Ryall in Neuropoisons: Their Pathophysiological Actions vol. 2, L. L. Simpson, D. R. Curtis, Eds. (Plenum, New York, 1974) pp 61-97; N. L. Benowitz, Ann. Rev. Med. 37, 21-32 (1986). Clinical trial of long-term efficacy in smoking cessation: T. Blondal et al., Brit. Med. J. 318, 285 (1999). Review of clinical experience in Tourette syndrome: A. A. Silver et al., CNS Spectrums 4, 68-76 (1999).
Properties: Colorless to pale yellow, oily liq; very hygroscopic; turns brown on exposure to air or light. Acrid burning taste. Develops odor of pyridine. bp745 247° (partial decompn); bp17 123-125°. Volatile with steam. nD20 1.5282. d420 1.00925. [a]D20 -169.3° (neat); [a]5461 -204.1°. pK1 (15°) 6.16; pK2 10.96. pH of 0.05M soln: 10.2. Forms salts with almost any acid and double salts with many metals and acids. Absorption spectrum: Purvis, J. Chem. Soc. 97, 1035 (1910); Dobbie, Fox, ibid. 103, 1194 (1913). Optical rotatory properties: T. M. Lowry, W. V. Lloyd, J. Chem. Soc. 1929, 1771. Misc with water below 60°; on mixing nicotine with water the volume contracts. Very sol in alc, chloroform, ether, petr ether, kerosene, oils. Distribution of nicotine between water and petroleum oils: Norton, Ind. Eng. Chem., Ind. Ed. 32, 241 (1940). LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod).
Boiling point: bp745 247° (partial decompn); bp17 123-125°
pKa: pK1 (15°) 6.16; pK2 10.96
Optical Rotation: [a]D20 -169.3° (neat); [a]5461 -204.1°
Index of refraction: nD20 1.5282
Density: d420 1.00925
Toxicity data: LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod)

Derivative Type: Hydrochloride
CAS Registry Number: 21361-93-3
Molecular Formula: C10H14N2.HCl
Molecular Weight: 198.70.
Percent Composition: C 60.45%, H 7.61%, N 14.10%, Cl 17.84%
Properties: Deliquesc crystals. [a]D20 +104° (p = 10).
Optical Rotation: [a]D20 +104° (p = 10)

Derivative Type: Dihydrochloride
CAS Registry Number: 6019-02-9
Molecular Formula: C10H14N2.2HCl
Molecular Weight: 235.16.
Percent Composition: C 51.08%, H 6.86%, N 11.91%, Cl 30.15%
Properties: Deliquesc crystals, very sol in water and alcohol. Nearly insol in ether.

Derivative Type: Sulfate
CAS Registry Number: 65-30-5
Additional Names: Nicotine neutral sulfate
Molecular Formula: (C10H14N2)2.H2SO4
Molecular Weight: 422.55.
Percent Composition: C 56.85%, H 7.16%, N 13.26%, S 7.59%, O 15.15%
Properties: Six-sided tablets. [a]D20 +88° (p = 70). Sol in water, alcohol.
Optical Rotation: [a]D20 +88° (p = 70)

Derivative Type: Bitartrate
CAS Registry Number: 65-31-6
Additional Names: Nicotine tartrate
Molecular Formula: C10H14N2.2C4H6O6
Molecular Weight: 462.40.
Percent Composition: C 46.75%, H 5.67%, N 6.06%, O 41.52%
Properties: Dihydrate, crystals. mp 90°. [a]D20 +26° (c = 10). Very sol in water or alcohol.
Melting point: mp 90°
Optical Rotation: [a]D20 +26° (c = 10)

Derivative Type: Zinc chloride double salt monohydrate
Molecular Formula: C10H16Cl4N2Zn.H2O
Molecular Weight: 389.49.
Percent Composition: C 30.84%, H 4.67%, Cl 36.41%, N 7.19%, Zn 16.79%, O 4.11%
Properties: Also with 4H2O. Very sol in water; sparingly sol in abs alcohol and ether.

Derivative Type: Salicylate
CAS Registry Number: 29790-52-1
Trademarks: Eudermol
Molecular Formula: C17H20N2O3
Molecular Weight: 300.35.
Percent Composition: C 67.98%, H 6.71%, N 9.33%, O 15.98%
Properties: Six-sided plates, mp 118°. [a]D20 +13° (c = 9). Freely sol in water or alcohol.
Melting point: mp 118°
Optical Rotation: [a]D20 +13° (c = 9)

Derivative Type: Polacrilex
CAS Registry Number: 96055-45-7
Trademarks: Nicorette (HMR)
Literature References: Prepn: S. Lichtneckert et al., DE 2136119; eidem, US 3901248 (1972, 1975 both to AB Leo). Review of efficacy in smoking cessation: K. O. Fagerström, Prog. Clin. Biol. Res. 261, 109-128 (1988).

CAUTION: Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Potential symptoms of overexposure are nausea, salivation, abdominal pain, vomiting, diarrhea; headache, dizziness, auditory and visual disturbances; confusion, weakness, incoordination; paroxysmal atrial fibrillation; convulsions, dyspnea. Death may result from paralysis of respiratory muscles. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 224; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 311-314.
Use: Insecticide; fumigant. In the U.S. a 40% soln of nicotine sulfate, Black Leaf 40, was the commonly used form. As a contact poison it is most effective as soap, i.e., as the laurate, oleate, or naphthenate. As a stomach poison a combination with bentonite has come into use.
Therap-Cat: Treatment of smoking withdrawal syndrome.
Therap-Cat-Vet: Ectoparasiticide. Has been used as an anthelmintic.
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Old 11-07-2008, 06:21 AM   #9
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I have had beers and wines with a slight tabacco taste. I have found in very small amounts this is almost identical to slight leathery tastes in wines. I would imagine that it is an oak attributed taste but not sure as to what extent of toasting you would do to some cubes to attribute it. I would almost thing a medium char for a slight amount of time in secondary could contribute to that taste. with a belgian yeast maybe? I have noticed it more in belgians that and other "region" as far as beer.

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Old 11-07-2008, 05:31 PM   #10
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Since you can't put your grains through the same process that maduros go though, unless you can get your grains to ferment in the sun, the other option would be to fake it. Some cigar companies dye their maduro cigars and add sugar to the dye to sweeten the flavor. Of course the dye is just for color and would be pointless in your case.

Maybe you could smoke your own grains .. just blow your cigar smoke on 'em.

As a cigar smoker myself, I would find it very unpleasant to drink some cigar nicotine, but could see myself enjoying some tobacco flavor.

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